Isoamyl Nitrite → HCID 67084010, compound

HRID 79007Notes

Reaction equation

HRID 79007 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([CH3:11])[C:5]=1[Cl:12].C(O[N:20]=O)CC(C)C>C(O)(=O)C>[CH3:1][O:2][C:3]([C:4]1[C:5]([Cl:12])=[C:6]2[C:7](=[CH:8][CH:9]=1)[NH:10][N:20]=[CH:11]2)=[O:13]

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 67083635HCID 67083635, compound

Product 1

HCID 67084010HCID 67084010, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-amino-2-chloro-3-methyl-benzoic acid methyl ester (5.29 g, 26.5 mmol) in acetic acid (100 mL) was added isoamylnitrite (3.9 mL, 29.2 mmol). The reaction mixture was stirred at room temperature for 30 minutes then heated at reflux for 3 hours. The reaction mixture was concentrated in vacuo and the resultant residue subjected to flash chromatography (SiO2, gradient 0-100% ethyl acetate in cyclohexane) to yield the title compound as an off-white solid (2.26 g, 40%). 1H NMR (CDCl3, 400 MHz) 3.97 (3H, s), 7.42 (1H, d, J=8.8 Hz), 7.95 (1H, d, J=8.8 Hz), 8.29 (1H, s).

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-72a07da25f844ac1b0aaad77fd82bccd
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

Loading…