Cyclopropylamine → N-cyclopropyl-2-hydroxybenzamide

HRID 456397Notes

Reaction equation

HRID 456397 reaction equation
C[O:2][C:3]1[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:5]([O-:7])=O.[CH:12]1([NH2:15])[CH2:14][CH2:13]1>C1(C)C=CC=CC=1>[CH:12]1([NH:15][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=2[OH:2])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 69828Cyclopropylamine2×HCID 6950218Benzoic acid, 2-methoxy-, ion(1-)

Product 1

HCID 822771N-cyclopropyl-2-hydroxybenzamideYield 53.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methylsalicylate (4.36 g, 28.69 mmol) and cyclopropylamine (1.64 g, 28.69 mmol) was heated at 80–100° C. for 3 h. An additional 0.5 equivalent of cyclopropylamine was added and the reaction mixture was kept at 70° C. for overnight. The reaction mixture was co-evaporated with toluene and the residue was purified by silica gel flash chromatography to give the subtitle compound (2.71 g).

Workup

  1. temperaturewas heated at 80–100° C. for 3 h
  2. customthe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-740826eff3a74334a73f1cecb41741a3
Source dataset
uspto-grants-2007_03
Patent number
US07186718B2

Reaction notes

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