GB318315A - The manufacture of ortho-hydroxy-benzyl-amine arsinic acids and their aroyl-derivatives - Google Patents
The manufacture of ortho-hydroxy-benzyl-amine arsinic acids and their aroyl-derivativesInfo
- Publication number
- GB318315A GB318315A GB16349/28A GB1634928A GB318315A GB 318315 A GB318315 A GB 318315A GB 16349/28 A GB16349/28 A GB 16349/28A GB 1634928 A GB1634928 A GB 1634928A GB 318315 A GB318315 A GB 318315A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- hydroxy
- arsinic
- hydroxyphenylarsinic
- prepared
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 4
- 239000001117 sulphuric acid Substances 0.000 abstract 4
- 235000011149 sulphuric acid Nutrition 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- -1 p-nitrophenol compound Chemical class 0.000 abstract 3
- 239000007858 starting material Substances 0.000 abstract 3
- PVACDNXAICDVIC-UHFFFAOYSA-N (4-hydroxyphenyl)arsinic acid Chemical compound OC1=CC=C(C=C1)[AsH](O)=O PVACDNXAICDVIC-UHFFFAOYSA-N 0.000 abstract 2
- KPRZOPQOBJRYSW-UHFFFAOYSA-N 2-(aminomethyl)phenol Chemical compound NCC1=CC=CC=C1O KPRZOPQOBJRYSW-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- MNSGOOCAMMSKGI-UHFFFAOYSA-N N-(hydroxymethyl)phthalimide Chemical compound C1=CC=C2C(=O)N(CO)C(=O)C2=C1 MNSGOOCAMMSKGI-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- VJWWIRSVNSXUAC-UHFFFAOYSA-N arsinic acid Chemical group O[AsH2]=O VJWWIRSVNSXUAC-UHFFFAOYSA-N 0.000 abstract 2
- 238000007127 saponification reaction Methods 0.000 abstract 2
- PTLRDCMBXHILCL-UHFFFAOYSA-M sodium arsenite Chemical compound [Na+].[O-][As]=O PTLRDCMBXHILCL-UHFFFAOYSA-M 0.000 abstract 2
- KDQPMQNHVQVVMR-UHFFFAOYSA-N 2-methyl-4-nitrophenol Chemical compound CC1=CC([N+]([O-])=O)=CC=C1O KDQPMQNHVQVVMR-UHFFFAOYSA-N 0.000 abstract 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 abstract 1
- HPJZUVCAEGIVAY-UHFFFAOYSA-N CC=1C=C(C=CC1O)[AsH](O)=O Chemical compound CC=1C=C(C=CC1O)[AsH](O)=O HPJZUVCAEGIVAY-UHFFFAOYSA-N 0.000 abstract 1
- SYJWGWOMFDYONN-UHFFFAOYSA-N ClC=1C=C(C=CC1O)[AsH](O)=O Chemical compound ClC=1C=C(C=CC1O)[AsH](O)=O SYJWGWOMFDYONN-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000003435 aroyl group Chemical group 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- UOUBPDZUBVJZOQ-UHFFFAOYSA-N n-(hydroxymethyl)benzamide Chemical compound OCNC(=O)C1=CC=CC=C1 UOUBPDZUBVJZOQ-UHFFFAOYSA-N 0.000 abstract 1
- VZUIPQDFDOKBSZ-UHFFFAOYSA-N n-[(5-amino-2-hydroxyphenyl)methyl]benzamide Chemical compound NC1=CC=C(O)C(CNC(=O)C=2C=CC=CC=2)=C1 VZUIPQDFDOKBSZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
- C07F9/74—Aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
318,315. Carpmael, A., (I. G. Farbenindustrie Akt.-Ges.). June 5, 1928. 2-Hydroxbenzylamine-5-arsinic acids and their aroyl derivatives.-2-Hydroxy-benzylaroylamine 5-arsinic acids of the formula and Y indicates hydrogen or a monovalent substituent are prepared either by (1) condensing a 1-hydroxy-4-phenylarsinic acid compound with a hydroxymethylaroylamine of the formula OH.CH2.NX, or (2) replacing the amino group of a 5-amino-2-hydroxy-benzylaroylamine by the arsinic acid group in known manner. The starting material for the first process may be obtained by replacing the nitro group of a p-nitrophenol compound by the arsinic acid group in known manner, whilst the starting material for the second process may be prepared by condensing a p-nitrophenol compound with a hydroxymethylaroylamine and reducing; in each case therefore a p-nitrophenol compound may function as starting material. The final products, and the corresponding 2-hydroxy-benzylamine - 5 - arsinic acids obtained by saponification, are useful therapeutically or in the manufacture of therapeutic compounds. According to the examples, (1) 2-hydroxy-benzylbenzoylamine-5-arsinic acid is prepared by condensing p-hydroxyphenylarsinic acid with hydroxymethyl-benzoylamine in the presence of sulphuric acid, or by diazotizing 5- amino-2-hydroxy-benzylbenzoylamine and treating with sodium arsenite and copper sulphate; boiling the product with caustic soda gives the 2-hydroxybenzylamine-5-arsinic acid; (2) 2-hydroxy-benzylphthalimide-5-arsinic acid results when 4-hydroxyphenylarsinic acid is treated with hydroxymethylphthalimide in the presence of sulphuric acid, or when p-nitrophenol is condensed with hydroxymethyl-phthalimide in the presence of sulphuric acid, and the product reduced with iron and acetic acid, diazotized and treated with sodium arsenite; by saponification it yields the product of the preceding example; (3) 2-hydroxy-3-methylbenzylphthalimide-5-arsinic acid and the corresponding 2 - hydroxy - 3 - methyl-benzylamine-5- arsinic acid are obtained from either 3-methyl-4- hydroxyphenylarsinic acid or 1-hydroxy-2-methyl- 4-nitrobenzene by the methods of the preceding example; (4) 3-chloro-2-hydroxy-benzylphthalimide-5-arsinic acid is prepared by the sulphuric acid condensation of 3-chloro-4-hydroxyphenylarsinic acid with hydroxymethyl-1-phthalmide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB16349/28A GB318315A (en) | 1928-06-05 | 1928-06-05 | The manufacture of ortho-hydroxy-benzyl-amine arsinic acids and their aroyl-derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB16349/28A GB318315A (en) | 1928-06-05 | 1928-06-05 | The manufacture of ortho-hydroxy-benzyl-amine arsinic acids and their aroyl-derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB318315A true GB318315A (en) | 1929-09-05 |
Family
ID=10075670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16349/28A Expired GB318315A (en) | 1928-06-05 | 1928-06-05 | The manufacture of ortho-hydroxy-benzyl-amine arsinic acids and their aroyl-derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB318315A (en) |
-
1928
- 1928-06-05 GB GB16349/28A patent/GB318315A/en not_active Expired
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