Methylamine → N,N-dimethyl-4-(2-nitroethenyl)aniline

HRID 55909

반응식

HRID 55909 반응식
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[N+:12]([C:15]1C=CC=CC=1)([O-:14])=[O:13].CN>CO>[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH:15][N+:12]([O-:14])=[O:13])=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 6329MethylamineHCID 7416NitrobenzeneHCID 74794-(Dimethylamino)Benzaldehyde

생성물 1

HCID 220551N,N-dimethyl-4-(2-nitroethenyl)aniline수율 41.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 4-dimethylaminobenzaldehyde (1.5 g, 10 mmol) in 3 mL methanol, 0.61 g (10 mmol) nitrobenzene and 0.15 mL of 22% methylamine aqueous solution was stirred for 3 days. The dark red solid obtained after filtration was recrystallized from nitromethane and rinsed with cold methanol to yield 0.79 g (41.1%) of red crystals, mp 180.6-180.9° C. (ref mp 181° C. (see Richter-Egger, D. L. et al. J. Chem. Educ. 2001, 78, 1375-1378)). 1H NMR 3.08 (s, 6H, Ar—N(CH3)2); 6.68 (2H, d, JHH 8.7 Hz, Ar—H); 7.43 (2H, d, JHH 9.0 Hz, Ar—H); 7.50 (1H, d, JHH 13.2 Hz, Ar—CH); 7.97 (1H, d, JHH 13.5 Hz, CH—NO2).

후처리

  1. customThe dark red solid obtained
  2. filtrationafter filtration
  3. customwas recrystallized from nitromethane
  4. washrinsed with cold methanol

출처 및 근거

ORD 기록
ord-3c6f54a8943f4e9a915438b1c3e3d041
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09433895B2

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