7-Nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline → 1-(7-Amino-3,4-dihydroquinolin-1(2H)-yl)-2,2,2-trifluoroethanone

HRID 494173

反応式

HRID 494173 の反応式
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][N:11]2[C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[CH:6][CH:5]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][N:11]2[C:14](=[O:19])[C:15]([F:18])([F:16])[F:17])=[CH:6][CH:5]=1

参加物

4

反応物 1

HCID 125783617-Nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline

生成物 1

HCID 820484221-(7-Amino-3,4-dihydroquinolin-1(2H)-yl)-2,2,2-trifluoroethanone収率 96%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A mixture of 7-nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline (D4) (1.51 g, 5.5 mmol) and 10% palladium on charcoal (150 mg, 54% water) in methanol (80 ml) was hydrogenated at atmospheric pressure and ambient temperature for 24 h. The catalyst was removed by filtration and was washed with further methanol. The combined filtrated and washings were concentrated in vacuo to give the title compound as a pale orange solid (1.29 g). 1H NMR (250 MHz, CDCl3) δ (ppm): 7.05 (br, 1H), 6.95 (d, 1H), 6.54 (dd, 1H), 3.78 (m, 2H), 3.65 (br, 2H), 2.74 (br, 2H), 2.03 (m, 2H).

後処理

  1. customThe catalyst was removed by filtration
  2. washwas washed with further methanol
  3. filtrationThe combined filtrated
  4. concentrationwashings were concentrated in vacuo

出典と根拠

ORDレコード
ord-3f558095e0f045e4a530bc8a8a7e2b1f
出典データセット
uspto-grants-2009_05
特許番号
US07538121B2

関連ノート

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