Acetic Acid → Methylamine

HRID 378976Notes

Reaction equation

HRID 378976 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][C:14]=2[O:21][CH3:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.C(O)(=O)C.[N+:30]([CH3:33])([O-:32])=[O:31]>CO>[CH3:33][NH2:30].[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[CH:33][N+:30]([O-:32])=[O:31])=[CH:15][C:14]=2[O:21][CH3:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 6375NitromethaneHCID 216972874-(5-Phenylpentyloxy)-3-methoxy-benzaldehyde

Product 2

HCID 6329MethylamineHCID 541505081-(5-Phenylpentyloxy)-2-methoxy-4-(2-nitro-vinyl)-benzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Operating analogously to example 2 using 4-(5-phenylpentyloxy)-3-methoxy-benzaldehyde (21 g, 73.4 mmoles), obtained as described in example 21, in methanol (86 ml), 8.03M methylamine in ethanol (1.92 ml, 15.4 mmoles), acetic acid (0.88 ml, 15.4 mmoles) and nitromethane (4.34 ml, 80.7 mmoles) 20 g of the title product were obtained (yield: 80%).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-f98f33e9f9bd44ef92de8a8a996bd8e0
Source dataset
uspto-grants-2001_10
Patent number
US06297257B1

Reaction notes

Loading…