Dimethylformamide dimethyl acetal → 5-(2-Dimethylamino-vinyl)-2,4-dinitro-benzoic acid ethyl ester

HRID 1915283Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16])[CH3:2].CO[CH:21]([N:24]([CH3:26])[CH3:25])OC>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[C:9]([CH:11]=[CH:21][N:24]([CH3:26])[CH3:25])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-methyl-2,4-dinitro-benzoic acid ethyl ester (39 g, 0.15 mol) and dimethoxymethyl-dimethylamine (32 g, 0.27 mol) in DMF (200 mL) was heated at 100° C. for 5 h. The mixture was poured into ice water. The precipitate was collected via filtration and washed with water to afford 5-(2-dimethylamino-vinyl)-2,4-dinitro-benzoic acid ethyl ester (15 g, 28%).

Workup

filtrationThe precipitate was collected via filtration
washwashed with water

Sources & evidence

ORD record: ord-462fc63d46724a1e8c68e1af84cf8b7d
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614327B2

Reaction notes

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