Ethanol → N-(5-Hydroxymethyl-2-methylphenyl)-3-nitrobenzamide

HRID 965129

Reaction equation

HRID 965129 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[CH2:5][OH:6].N1C=CC=CC=1.[N+:17]([C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24])([O-:19])=[O:18].CCO>C1COCC1>[OH:6][CH2:5][C:4]1[CH:7]=[CH:8][C:9]([CH3:10])=[C:2]([NH:1][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][CH:28]=[C:20]([N+:17]([O-:19])=[O:18])[CH:21]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 8495Benzoyl chloride, 3-nitro-HCID 586243(3-Amino-4-methylphenyl)methanol

Product 1

HCID 19074226N-(5-Hydroxymethyl-2-methylphenyl)-3-nitrobenzamideYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred, cooled (0° C.) mixture of 3-amino-4-methylbenzyl alcohol (10.0 g, 0.072 mol) and pyridine (5.8 g, 0.072 mol) in THF (100 ML) was added 3-nitrobenzoyl chloride (13.5 g, 0.072 mol). After 2 h, the mixture was concentrated, suspended in water and filtered to give a brown solid. Trituration with hot EtOH gave 18.8 g (90%) of product as a white solid, mp 198°-200° C.; 1H NMR (DMSO-d6) δ 2.20 (s, 3 H), 4.46 (s, 2 H), 7.12 (dd, J=7.8 Hz, 1.5 Hz, 1 H), 7.25 (dd, J=7.8, 1.5 Hz, 1 H), 7.82 (m, 1 H), 8.41 (m, 2 H), 8.78 (s, 1 H), 10.26 (s, 1 H).

Workup

  1. temperatureTo a stirred, cooled
  2. concentrationthe mixture was concentrated
  3. filtrationfiltered
  4. customto give a brown solid

Sources & evidence

ORD record
ord-fbac06a374d14c68b1c2773bee06949d
Source dataset
uspto-grants-1998_06
Patent number
US05773420

Linked notes

Loading…