Phenyl chloroformate → HCID 9794992, compound

HRID 330774Notes

Reaction equation

HRID 330774 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=O>N1C=CC=CC=1>[CH3:11][C:8]1[CH:9]=[CH:10][C:2]2[N:1]=[C:13]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 762552-Amino-5-methylbenzoic acid

Product 1

HCID 9794992HCID 9794992, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-amino-5-methylbenzoic acid (1.0 g, 6.6 mmol) in pyridine (10 ml) was cooled to 0° C. and treated dropwise with phenyl chloroformate (3.3 ml, 26 mmol). The resulting mixture was allowed to warm to room temperature and stirred for 16 h, after which time the pyridine was removed in vacuo. The residue was washed with water (20 ml) and dried in vacuo. Recrystallisation from toluene afforded the desired product as a pale brown solid (692 mg, 41%); δH (400 MHz, DMSO-d6) 2.40 (3H, s, CH3), 7.33-7.45 (3H, m, Ph), 7.48-7.55 (3H, m, Ph), 7.63 (1H, d, J 8, Ph), 7.89 (1H, s, Ph-H5); m/z (ES+) 254 (MH+).

Workup

  1. customafter which time the pyridine was removed in vacuo
  2. washThe residue was washed with water (20 ml)
  3. customdried in vacuo
  4. customRecrystallisation from toluene

Sources & evidence

ORD record
ord-e629b6f7b91c4ce9b25a9ba3ab41b648
Source dataset
uspto-grants-2014_11
Patent number
US08877750B2

Reaction notes

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