HCID 15052973, compound → HCID 431943, compound
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:11][C:12]([OH:14])=[O:13])[CH:7]=[CH:8][C:9]=1[NH2:10])([O-])=O>[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:11][C:12]([OH:14])=[O:13])[CH:7]=[CH:8][C:9]=1[NH2:10]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
2-(3,4-Diaminophenyl)acetic acid can be prepared by acetylation of 2-(4-aminophenylacetonitrile with acetic anhydride in pyridine. The 2-(4-acetamidophenyl)acetonitrile product is nitrated in acetic anhydride to provide 2-(3-nitrile-4-acetamidophenyl)acetonitrile. The nitrile is hydrolyzed with concentrated hydrochloric acid to give 2-(3-nitro-4-aminophenyl)acetic acid after neutralization. The nitro acid is then hydrogenated at 60 psi at room temperature over palladium-on-carbon to yield 2-(3,4-diaminophenyl)acetic acid. The acid can be esterified with C1 -C8 carbinols in the presence of acid catalysts to yield starting materials according to II in which R3 is an ester group. Similarly, the preparation of 2-(3,4-diaminophenyl)propionic acid begins with 2-(4-aminophenyl)propionitrile as described above for the preparation of the diaminophenylacetic acid.
Sources & evidence
- ORD record
- ord-0a26df94fabe4604a9f4957d2ad78b41
- Source dataset
- uspto-grants-1977_04
- Patent number
- US04018790
Reaction notes
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