Methylamine → 4-(2-hydroxyphenyl)-N-methylbutyramide

HRID 1176398Notes

Reaction equation

HRID 1176398 reaction equation
[O:1]1[C:7](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[CH3:13][NH2:14]>C(O)(C)C>[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH2:4][CH2:5][CH2:6][C:7]([NH:14][CH3:13])=[O:8]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 109757954,5-Dihydrobenzo[b]oxepin-2(3H)-one

Product 1

HCID 685011294-(2-hydroxyphenyl)-N-methylbutyramide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 1.0 g of 4,5-dihydro-3H-benzo[b]oxepin-2-one and 40 ml of 10% methylamine in isopropanol is heated in an autoclave at 100° C. over 16 hours. The reaction mixture is cooled to room temperature and concentrated by evaporation. The title compound is obtained as white crystals from the residue by means of flash chromatography (SiO2 60F). Rf=0.20 (4:1 EtOAc-heptane); Rt=2.66.

Workup

  1. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-46c0c9a46292460a8488aa84ee483bde
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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