TW322472B - - Google Patents

Download PDF

Info

Publication number
TW322472B
TW322472B TW085108609A TW85108609A TW322472B TW 322472 B TW322472 B TW 322472B TW 085108609 A TW085108609 A TW 085108609A TW 85108609 A TW85108609 A TW 85108609A TW 322472 B TW322472 B TW 322472B
Authority
TW
Taiwan
Prior art keywords
sodium hydroxide
patent application
copper
item
reaction
Prior art date
Application number
TW085108609A
Other languages
English (en)
Original Assignee
American Cyanamid Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Application granted granted Critical
Publication of TW322472B publication Critical patent/TW322472B/zh

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8
    • C07D215/26—Alcohols; Ethers thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Quinoline Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Description

A7 B7
五、發明説明（ 發明之概述 本發明係關於在铜催化劑存在下，轉化經取代之8·氣喳 啦至經取代之8-羥喹琳之方法。化合物8-瘦基-3-甲氧基甲 喳啉是本方法之產物，其爲咪唑啉酮除草劑I之前驅物。
發明之詳細説明 本發明係以塵力反應器方法製備經取代之幾啥琳，如 下所示：
+ <N±水溶液 銅催化劑 150° -200V
其中R爲CrC4虎基，羥基-CrC4虎基，crc4_故氧基 燒基’ c rC4鹵烷基，或二· c rC4燒胺基-c rc4燒基 1 C 化合物8-羥基-3-甲氧基甲喹啉可根據本發 乃方法製播 其爲合成咪唑啉酮除草劑I乏中間物，如下所示. 〜’ -4 - 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） ( Γ---疼------.π—I"^----Φ, (請先閱讀背面之注意事項再广-*1本頁) 一 經濟部中央榡準局員工消費合作社印製 五 、發明説明（
(過氧化作用）
I A7 B7
— ^ ^ 批衣-- (請先閱讀背面之注意事項再广.，½本頁) 上述係敎示於雷克（W. F. Reiker)及丹尼爾（w A Daniel 之美國專利第4,816,588號（1989年）’發明名稱爲"呲啶/ 2,3 一幾酸之製法，及露斯（仏如仍L〇s)之美國專利第 4,798,619號（1989年），發明名稱爲"2_(2_咪唑啉_2_基）吡啶 及-喹啉及該化合物作爲除草劑之用途.·。 下列實例係用以説明本發明，但不以此限制本發明。 實例1 將4.15克之8-氣-3-甲氧基甲》奎淋（2〇毫莫耳），8 〇克之 50%氫氧化鈉溶液（1〇〇毫莫耳）及在95毫升水中含25〇毫克 之五水硫酸铜（1.0毫莫耳，5莫耳百分比）之溶液置入一容 量爲600毫升之钽材質之經擭拌帕（parr)壓力反應器。氫氧 化鈉之濃度爲4。/。。系統爲密封，升溫至16〇»c且維持21 5 小時》經冷卻溶液以赛力特矽藻土（Ce〗ite)過濾，並以二份 20毫升之甲苯萃取’接著以硫酸調整水溶液層之pH至3-4 5- 本紙張尺度適用宁國國家標準（CNS ) A4規格 訂 經濟部辛央標準局員工消費合作社印製 m--_--------------- 1- I - I · A7 B7 〇22472 五、發明説明（ -----—. 3 經濟部中央標準局員工消費合作杜印製 ，最後以氫氧化銨調整pH至7。混合物以二份5〇毫升之乙 酸乙酯萃取。旋轉蒸發有機層得到2 39克（63%產率）黃綠 色固體之粗8-羥基-3-甲氧基甲喳啉。以二份5〇〇毫升之沸 水處理該粗物質，留下一些不溶物。分離長且似絲的黃色 針狀物之純8-羥基-3-甲氧基甲喹啉。經由過濾及乾燥後得 到1·83克（48%產率）。 實例2 以相同方法重複實例1之反應、，除了使用1 95毫升的水， 因此氫氧化鈉之濃度爲2%。此類似之方法得到2.56克（68% 產率）之粗8-超基-3 -甲氧基甲峡啦。從熱水中再結晶可得 到1.92克（51%產率）之純物質。 實例3 以一較大規模且經修正之方法重複實例i之反應。將311 克之8-氣-3-甲氧基甲喹啉（150毫莫耳），60克之50%氫氧化 鈉水溶液（750毫莫耳）及在1460毫升水中含1.87克之五水硫 酸銅（7.5毫莫耳，5莫耳百分比）之溶液置入一容量爲一加 侖之#316不銹鲷材質之經攪拌鈕帕（parr)譽力反應器。系 統爲密封，升溫至160°C且維持17小時。經冷卻溶液以賽 力特矽藻土（Celite)過濾，接者在冰浴中徹底急冷。以50毫 升濃鹽酸調整pH至4，再以約5毫升氫氧化銨調整pH至8 » 過濾產生之沈澱物並以水洗滌。在6(TC眞空烘箱中乾燥產 物過夜後得到19.64克灰綠包粉末之粗8-羥基-3-甲氧基甲 喹啉（69%產率）。以三份250毫升之乙酸乙酯萃取濾液。旋轉蒸 發有機層得到4.10克深綠色油之粗產物（14%產率，因此總粗產 -6- 本紙張尺度適用中囷國家標隼（CNS ) A4規格（210X 297公釐） _^ΐτ—--^----.^ {請先閱讀背面之注意事項再一本萸) ( 322472 : 五、發明説明（4 ) 率爲83%)。從熱水中再結晶該油可得到124克黃綠色針狀之純 產物。 實例4 將一等份之五水硫酸銅與二等份之8•羥基_3_〒氧基甲喳 啉在過量氫氧化鈉水溶液中反應以製備8_羥基_3_甲氧基曱 喳啦之銅錯合物。過濾經沈澱之綠色粉末，以水洗滌並乾 燥至伍重。重複實例3之反應，以1.5莫耳百分比之8·羥基-3-甲氧基甲喹啉之銅錯合物取-代〗莫耳百分比之硫酸銅。 類似之方法得到80°/。產率之第一堆產物及u %產率額外之 第二堆產物’因此總粗產率爲91 % β 實例5 使用1.0莫耳百分比之8_羥基_3_甲氧基甲喹啉之銅錯合物 重複實例4之反應《總粗產率爲92%β將濃鹽酸添加至粗 產物之丙酮溶液以沈澱氩氣鹽，以藉此純化產物。氫氣鹽 之總產量爲58。/。。 實例6 以相同方法重複實例5之反應。總粗產率爲94%β分析產 物顯示眞實產率爲78%。 ----：I-^----t.------、玎|1;----^ (請先閱讀背面之注意事項再t 本頁) 一 經濟部中央標準局員工消费合作社印製 本纸張尺度適用 rm¥k·^ ( cns ) A4^717^l97/>i7

Claims (1)

  1. 3224*713第85108609號專利申請案 中文申請專利年-^ A8 Bg 六、申請專利範I 86.10. 2 1 1. 一種製備經取代之8-羥喳啉之方法，其包括在攪拌之 加 屋反應器中，由式
    之經取代之8 -氣p奎淋 與稀絵性溶液’在銅催·化:劑存—在下且溫度在l5〇_2〇〇»C 範圍内反應，式中R爲C丨·C4_烷氧基C丨·(：4烷基。 2 ·根據申請專利範圍第1項之方法，其中銅催化劑爲銅 鹽或有機銅錯合物，且鹼性溶液爲氫氧化鈉。 3 .根據申請專利範圍第2項之方法，其中8 _氣_ 3 -甲氧基 甲喹啉被轉化爲8-羥基-3-甲氧基甲喳啉。 4.根據申請專利範圍第3項之方法，其中催化劑爲i莫耳 百分比之有機銅錯合物，其係由硫酸銅與8_羥基-3-甲 氧基甲喳啉之反應製備，且氫氧化鈉爲5等份2%氫氧 化鈉水溶液，其中反應係在溫度爲16〇-c下攪拌丨了至以 小時。 5 .根據申請專利範圍第3項之方法，其中催化劑爲5莫耳 百分比之硫酸銅，且氫氧化鈉爲5等份2%至4%氫氧化 鈉水溶液’其中反應係在溫度爲16〇-c下攪拌17至22 小時。 6.根據申請專利範圍第5項之方法，其中氫氧化納爲亏等 份2 %氯氧化納水溶液。 i紙張以適用中S®家揉準（CNS〉( 21()><297公董）- (請先H讀背面之注意事項再填寫本頁) 訂 » In 1^1 an
TW085108609A 1995-05-24 1996-07-16 TW322472B (zh)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US08/448,693 US5597924A (en) 1995-05-24 1995-05-24 Coversion of substituted 8-chloroquinolines to substituted 8-hydroxyquinolines

Publications (1)

Publication Number Publication Date
TW322472B true TW322472B (zh) 1997-12-11

Family

ID=23781301

Family Applications (1)

Application Number Title Priority Date Filing Date
TW085108609A TW322472B (zh) 1995-05-24 1996-07-16

Country Status (26)

Country Link
US (1) US5597924A (zh)
EP (1) EP0744399B1 (zh)
JP (1) JPH093048A (zh)
KR (1) KR960041165A (zh)
CN (1) CN1067380C (zh)
AR (1) AR002088A1 (zh)
AT (1) ATE197147T1 (zh)
AU (1) AU707068B2 (zh)
BR (1) BR9602397A (zh)
CA (1) CA2177106A1 (zh)
CZ (1) CZ289101B6 (zh)
DE (1) DE69610739T2 (zh)
DK (1) DK0744399T3 (zh)
ES (1) ES2152490T3 (zh)
GR (1) GR3035177T3 (zh)
HU (1) HU216070B (zh)
IL (1) IL118351A (zh)
IN (1) IN181570B (zh)
PT (1) PT744399E (zh)
RU (1) RU2160255C2 (zh)
SG (1) SG43368A1 (zh)
SI (1) SI0744399T1 (zh)
SK (1) SK65696A3 (zh)
TR (1) TR199600434A1 (zh)
TW (1) TW322472B (zh)
YU (1) YU30696A (zh)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008022221A1 (de) 2008-05-06 2009-11-12 Universität des Saarlandes Inhibitoren der humanen Aldosteronsynthase CYP11B2
US8541404B2 (en) * 2009-11-09 2013-09-24 Elexopharm Gmbh Inhibitors of the human aldosterone synthase CYP11B2
CN102787513A (zh) * 2012-07-24 2012-11-21 苏州市华元化工有限公司 一种高效螯合剂及其生产方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4854078A (zh) * 1971-11-16 1973-07-30
JPS5942535A (ja) * 1982-09-02 1984-03-09 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料
US4609734A (en) * 1983-11-08 1986-09-02 Lonza Ltd. Process for the production of 2-hydroxypyridines from 2-pyridine carboxylic acid-N-oxides
DE3614756A1 (de) * 1986-04-30 1987-11-05 Ruetgerswerke Ag Verfahren zur herstellung von 5-alkylchinolinsaeuren und mittel zur durchfuehrung des verfahrens
US4816588A (en) * 1986-09-12 1989-03-28 American Cyanamid Company Method for the preparation of pyridine-2,3-dicarboxylic acids
IL89142A (en) * 1988-03-10 1993-04-04 American Cyanamid Co Method for the sequential oxidation of substituted 8-hydroxyquinolines to produce substituted pyridine-2,3- dicarboxylic acids
US5281713A (en) * 1991-12-20 1994-01-25 American Cyanamid Company Process for the manufacture of 2-alkoxymethylacrolein

Also Published As

Publication number Publication date
DK0744399T3 (da) 2000-11-20
HUP9601393A3 (en) 1997-08-28
AU707068B2 (en) 1999-07-01
AR002088A1 (es) 1998-01-07
HU216070B (hu) 1999-04-28
MX9601818A (es) 1997-07-31
BR9602397A (pt) 1998-10-06
TR199600434A1 (tr) 1997-03-21
SG43368A1 (en) 1997-10-17
CZ139596A3 (en) 1996-12-11
ES2152490T3 (es) 2001-02-01
PT744399E (pt) 2001-03-30
SI0744399T1 (en) 2001-02-28
KR960041165A (ko) 1996-12-19
US5597924A (en) 1997-01-28
IL118351A (en) 2001-04-30
SK65696A3 (en) 1996-12-04
DE69610739T2 (de) 2001-05-23
ATE197147T1 (de) 2000-11-15
GR3035177T3 (en) 2001-04-30
CZ289101B6 (cs) 2001-11-14
HUP9601393A2 (en) 1997-04-28
EP0744399A2 (en) 1996-11-27
RU2160255C2 (ru) 2000-12-10
YU30696A (sh) 1998-12-23
EP0744399B1 (en) 2000-10-25
JPH093048A (ja) 1997-01-07
CA2177106A1 (en) 1996-11-25
CN1067380C (zh) 2001-06-20
CN1146989A (zh) 1997-04-09
IL118351A0 (en) 1996-09-12
DE69610739D1 (de) 2000-11-30
EP0744399A3 (en) 1997-05-07
HU9601393D0 (en) 1996-07-29
IN181570B (zh) 1998-07-11
AU5239896A (en) 1996-12-05

Similar Documents

Publication Publication Date Title
TW385305B (en) A process for preparing pyridine-2,6-diamines
JPS60149568A (ja) １−置換−５−ヒドロキシメチル−２−メルカプト−イミダゾ−ル類およびその製法
TW322472B (zh)
CN111574455A (zh) 一种二丙酸咪唑苯脲及其中间体的制备方法
JPH0830064B2 (ja) 高純度形のエブセレンの製造方法
EP0960879A2 (en) Improved process for the preparation of 5-aminotetrazole
CN108794468A (zh) 一种四氢吡啶并吲哚类化合物的制备方法
JPH0212229B2 (zh)
PL185421B1 (pl) Sposób wytwarzania pochodnych 4-amino-3-okso-2,3,4,5-tetrahydro-1,2,4-triazyny
CN113999171A (zh) 一种高含量双吡啶硫酮的合成方法
CN102558152A (zh) 4-[(3-亚甲基吡啶)-氨基]-6-甲基-4,5-二氢-2h-[1,2,4]三唑-3-酮的制备方法
US3118943A (en) Aminobenzylsulfonylethanol compounds
US4387253A (en) Preparation of dichlorobenzyl alcohol
US4853483A (en) Preparation of alkyl thiosemicarbazides
CN110698419A (zh) 一种轮环藤宁的制备方法
CZ292732B6 (cs) Způsob přípravy 3-amino-1,2,4-benzotriazin-1,4-dioxidu
CN114933567B (zh) 一种2-甲硫基-4-嘧啶酮的制备方法
CN114249703B (zh) 适合工业放大的医药中间体的制备方法
MXPA96001818A (en) Conversion of 8-chloroquinolines replaced a8-hydroxyquinolines sustitui
CN109651187B (zh) 一种(s)-n′-(2-苄氧基亚丙基)甲酰肼的合成方法
TW393471B (en) Process for the preparation of aminotriazine derivatives
US1558584A (en) Complex gold compound and process of making same
PL185411B1 (pl) Sposób wytwarzania pochodnych pirydyloaminotriazyny
CA2145022A1 (en) Process for the preparation of 5-formylaminopyrimidines
CN117384063A (zh) 一种三甲基肼的合成工艺及产品