Acetic Acid → 3-[4-Cyanobenzyl]aminobenzoic acid

HRID 726714Notes

Reaction equation

HRID 726714 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].[NH2:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([OH:17])=[O:16].C([BH3-])#N.[Na+].C(O)(=O)C>CN(C)C=O>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:11][C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=[O:16])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 74193-Aminobenzoic AcidHCID 660424-CyanobenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 197073993-[4-Cyanobenzyl]aminobenzoic acidYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-cyanobenzaldehyde (0.65 g; 5 mmoles), 3-aminobenzoic acid (0.68 g; 5 mmoles) and sodiumcyanoborohydride (0.35 g; 5 mmols) were stirred in N,N-dimethylformamide (25 ml) containing 1% acetic acid at room temperature for 2 hrs. The product was precipitated out by addition of water. The solid was filtered and dried in vacuo to give 0.95 g white solid. FAB-MS: MH+ =253.

Workup

  1. customThe product was precipitated out by addition of water
  2. filtrationThe solid was filtered
  3. customdried in vacuo

Sources & evidence

ORD record
ord-1606ef0ee9e846559855b749621dffd0
Source dataset
uspto-grants-1998_01
Patent number
US05710166

Reaction notes

Loading…