Dimethylformamide dimethyl acetal → Methyl 4-ethoxy-5-methoxy-2-(dimethylaminomethyleneamino)benzoate

HRID 612116

Reaction equation

[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[C:9]([O:15][CH3:16])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>CN(C=O)C.CC(N(C)C)=O>[CH2:13]([O:12][C:10]1[C:9]([O:15][CH3:16])=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([N:1]=[CH:19][N:20]([CH3:22])[CH3:21])[CH:11]=1)[CH3:14]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 15.056 g (66.9 mmol) methyl 2-amino-4-ethoxy-5-methoxybenzoate and 14.1 ml (100 mmol) N,N-dimethylformamide dimethylacetal was heated to 100° C. under N2. At 4.5 hours added 4.7 ml (33.3 mmol) more DMF/DMA and removed heat at 5 hours. Stripped solvent, azeotroped with toluene, and dried in vacuo, giving 18.211 g of grey-brown solid: mass spectrum (electrospray m/e): M+H=281.3.

Workup

customremoved
temperatureheat at 5 hours
customStripped solvent, azeotroped with toluene
customdried in vacuo

Sources & evidence

ORD record: ord-b625d53183804ba2bb7b702fdf150b11
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06002008

Linked notes

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