JPH0359904B2 - - Google Patents
Info
- Publication number
- JPH0359904B2 JPH0359904B2 JP8882683A JP8882683A JPH0359904B2 JP H0359904 B2 JPH0359904 B2 JP H0359904B2 JP 8882683 A JP8882683 A JP 8882683A JP 8882683 A JP8882683 A JP 8882683A JP H0359904 B2 JPH0359904 B2 JP H0359904B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- methyl
- producing
- sulfuric acid
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- -1 2,3-dihydro-4H-1,4-benzoxazin-4-yl Chemical group 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XJDDLMJULQGRLU-UHFFFAOYSA-N 1,3-dioxane-4,6-dione Chemical compound O=C1CC(=O)OCO1 XJDDLMJULQGRLU-UHFFFAOYSA-N 0.000 description 2
- QDEJGQKJMKXYLM-UHFFFAOYSA-N 2h-pyrido[2,3-h][1,2]benzoxazine Chemical class C1=CC2=NC=CC=C2C2=C1C=CNO2 QDEJGQKJMKXYLM-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- YILGXIZRZUDENO-UHFFFAOYSA-N 10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13),11-tetraene-11-carboxylic acid Chemical compound C1COC2=CC=CC3=C2N1C=C(C(=O)O)C3=O YILGXIZRZUDENO-UHFFFAOYSA-N 0.000 description 1
- KLTMALVMVMGIGT-UHFFFAOYSA-N 2-methyl-4h-1,4-benzoxazine Chemical compound C1=CC=C2OC(C)=CNC2=C1 KLTMALVMVMGIGT-UHFFFAOYSA-N 0.000 description 1
- BVHSAZFNVBBGNX-UHFFFAOYSA-N 7,8-difluoro-3-methyl-3,4-dihydro-2h-1,4-benzoxazine Chemical compound C1=CC(F)=C(F)C2=C1NC(C)CO2 BVHSAZFNVBBGNX-UHFFFAOYSA-N 0.000 description 1
- SNTZGENQEQKPHV-UHFFFAOYSA-N O1CC=NC2=CC(C(=O)OCC)=CC=C21 Chemical compound O1CC=NC2=CC(C(=O)OCC)=CC=C21 SNTZGENQEQKPHV-UHFFFAOYSA-N 0.000 description 1
- TZSXJUSNOOBBOP-UHFFFAOYSA-N ac1mwmhd Chemical compound CC1COC2=C(F)C(F)=CC3=C2N1C=C(C(=O)OCC)C3=O TZSXJUSNOOBBOP-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8882683A JPS59216890A (ja) | 1983-05-20 | 1983-05-20 | ピリドベンズオキサジン誘導体の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8882683A JPS59216890A (ja) | 1983-05-20 | 1983-05-20 | ピリドベンズオキサジン誘導体の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59216890A JPS59216890A (ja) | 1984-12-06 |
| JPH0359904B2 true JPH0359904B2 (pt) | 1991-09-12 |
Family
ID=13953736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8882683A Granted JPS59216890A (ja) | 1983-05-20 | 1983-05-20 | ピリドベンズオキサジン誘導体の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59216890A (pt) |
-
1983
- 1983-05-20 JP JP8882683A patent/JPS59216890A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59216890A (ja) | 1984-12-06 |
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