Propyl chloroformate → HCID 10176807, compound

HRID 330775Notes

Reaction equation

HRID 330775 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][CH2:16][CH2:17][CH3:18])=O>N1C=CC=CC=1>[CH2:16]([O:15][C:13]1[O:5][C:4](=[O:6])[C:3]2[CH:7]=[C:8]([CH3:11])[CH:9]=[CH:10][C:2]=2[N:1]=1)[CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 7998Propyl chloroformateHCID 762552-Amino-5-methylbenzoic acid

Product 1

HCID 10176807HCID 10176807, compoundYield 66.3%

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 propyl chloroformate (3.0 ml, 26 mmol). The resulting mixture was allowed to warm to room temperature and stirred for 4 h, after which time the pyridine was removed in vacuo. The residue was washed with water (25 ml) and dried in vacuo to afford the desired product as an off-white solid (0.96 g, 66%); δH (400 MHz, DMSO-d6) 1.03 (3H, t, J 7, CH2CH3), 1.82 (2H, tq, J, J′ 7, CH2CH3), 2.46 (3H, s, CH3), 4.42 (2H, t, J 7, OCH2), 7.40 (1H, d, J 8, Ph), 7.71 (1H, d, J 8, Ph), 7.89 (1H, s, Ph); m/z (ES+) 219 (MH+).

Workup

  1. customafter which time the pyridine was removed in vacuo
  2. washThe residue was washed with water (25 ml)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-591b25ae0ca74d188cb0de4209695c27
Source dataset
uspto-grants-2014_11
Patent number
US08877750B2

Reaction notes

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