Ammonia → 3-Amino-4-propylbenzoic acid

HRID 1385090Notes

Reaction equation

HRID 1385090 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH2:13][CH2:14][CH3:15])[C:7]([OH:9])=[O:8])([O-])=O.O.[K+].[Br-].N>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH2:13][CH2:14][CH3:15])[C:7]([OH:9])=[O:8]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 253877Potassium BromideHCID 155216373-Nitro-4-propylbenzoic acid

Product 1

HCID 155216383-Amino-4-propylbenzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1.96 g (57.2 mmol) 3-nitro-4-propyl-benzoic acid and 1.5 g 10% Pd/C, 50% water wet, in 250 mL CH3OH was placed on a Parr hydrogenation apparatus and shaken under 25 psi H2 at ambient temperature. After 1 h, the reaction mixture was filtered through Celite®, and the filtrate concentrated and dried to give 9.80 g (96%) of a pale yellow cyrstalline solid: mp 139.5-142.5° C.; IR (KBr) 3200−2400, 3369, 3298, 2969, 2874, 25588, 1690, 1426, 1260, 916, 864 cm−1; 1H NMR (300 MHz, DMSO-D6) δ 0.90 (t, 3H, J=7.2 Hz), 1.52 (m, 2H), 2.42 (m, 2H), 5.08 (br s, 2H), 6.96 (d, 1H, J=7.8 Hz), 7.05 (dd, 1H, J=1.7, 7.8 Hz), 7.20 (d, 1H, J=1.7 Hz); MS (Cl, NH3) m/z 180 (M+H+, base); Anal. calcd for C10H13NO2•⅓H2O; C, 64.85; N, 7.89; N, 7.56. Found: C, 64.69; H, 7.49; N, 7.86.

Workup

  1. filtrationthe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated
  3. customdried
  4. customto give 9.80 g (96%) of a pale yellow cyrstalline solid

Sources & evidence

ORD record
ord-f1de8d0dd5394d36a0e8348063ef071a
Source dataset
uspto-grants-2001_07
Patent number
US06262040B1

Reaction notes

Loading…