Dimethylformamide dimethyl acetal → (E)-Methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate

HRID 330134

反応式

HRID 330134 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>CN(C)C=O>[CH3:17][N:18]([CH3:20])/[CH:19]=[CH:1]/[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

参加物

4

反応物 2

HCID 78373Dimethylformamide dimethyl acetalHCID 81816Methyl 4-methyl-3-nitrobenzoate

生成物 1

HCID 894337(E)-Methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate収率 98%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of methyl 4-methyl-3-nitrobenzoate (4.46 g) in N,N-dimethylformamide (23 ml) was treated with N,N-dimethylformamide dimethyl acetal (8.18 g) and heated at 130° for 2 hours. The solvent was evaporated and the residue was triturated with ether to give methyl E-4-(2-dimethylaminovinyl)-3-nitrobenzoate (5.58 g, 98%) as a red powder; NMR (80 MHz, CDCl3): 2.98[s, 6H, N(CH3)2 ], 5.90(d, 1H, CHN), 7.14(d, 1H, CHCHN), 7.45(d, 1H, H5 -Ar), 7.90(dd, 1H, H6 -Ar), 8.47(d, 1H, H2 -Ar).

後処理

  1. temperatureheated at 130° for 2 hours
  2. customThe solvent was evaporated
  3. customthe residue was triturated with ether

出典と根拠

ORDレコード
ord-918763e0842942a7a7e96d47758d4e2d
出典データセット
uspto-grants-1990_01
特許番号
US04894386

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