Dimethylformamide dimethyl acetal → Methyl 4-dimethylaminovinyl-3-nitrobenzoate

HRID 1009967

반응식

HRID 1009967 반응식
[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=O)C>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([CH:1]=[CH:17][N:18]([CH3:20])[CH3:19])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1

참가 물질

4

반응물 2

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

생성물 1

HCID 894336Methyl 4-dimethylaminovinyl-3-nitrobenzoate수율 81.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
140 °C

실험 절차

Methyl 4-methyl-3-nitrobenzoate (5 g, 25.6 mmol) was dissolved in DMF (25 mL, 5 vol) and to this was added N,N-dimethylformamide dimethylacetal (4.4 mL, 33.3 mmol). The mixture was allowed to stir at 140° C. for 3 h. The resulting deep red solution was allowed to cool and concentrated under vacuum. The residue was triturated with methanol and filtered. The filtrate was washed with methanol and dried on the sinter to yield 4-(2-dimethylamino-vinyl)-3-nitrobenzoic acid methyl ester (5.2 g, 80%). 1H NMR (300 MHz, DMSO), δ: 2.98 (6H, s, 2×CH3), 3.87 (3H, s, CH3), 5.58 (1H, m, CH), 7.72-7.83 (3H, m, ArH), 8.32 (1H, m, CH).

후처리

  1. temperatureto cool
  2. concentrationconcentrated under vacuum
  3. customThe residue was triturated with methanol
  4. filtrationfiltered
  5. washThe filtrate was washed with methanol
  6. customdried on the sinter

출처 및 근거

ORD 기록
ord-6fa1c4137dfb46c28f449e090ba9fe03
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973181B2

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