1-Methyl-7-nitro-1,2,3,4-tetrahydroquinoline → 1-Methyl-1,2,3,4-tetrahydroquinolin-7-amine

HRID 494172ノート

反応式

HRID 494172 の反応式
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-])=O)[CH:10]=2)[CH2:5][CH2:4][CH2:3]1>[Pd].CO>[NH2:12][C:9]1[CH:10]=[C:11]2[C:6]([CH2:5][CH2:4][CH2:3][N:2]2[CH3:1])=[CH:7][CH:8]=1

参加物

4

反応物 1

HCID 114809551-Methyl-7-nitro-1,2,3,4-tetrahydroquinoline

生成物 1

HCID 112174211-Methyl-1,2,3,4-tetrahydroquinolin-7-amine収率 57%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A mixture of 1-methyl-7-nitro-1,2,3,4-tetrahydroquinoline (D2) (5.35 g, 27.9 mmol) and 10% palladium on charcoal (2 g, 54% water) in methanol (150 ml) was hydrogenated at atmospheric pressure and ambient temperature temperature for 3 d. The catalyst was filtered off and washed with further methanol. The combined filtrated and washings were concentrated in vacuo to give the crude product, which was purified by flash column chromatography. Elution with 5-10% EtOAc/DCM gave the title compound as a brown oil (2.58 g). 1H NMR (250 MHz, CDCl3) δ(ppm): 6.73 (dd, 1H), 5.99 (m, 2H), 3.49 (br, 1H), 3.18 (m, 2H), 2.84 (s, 3H), 2.66 (t, 2H), 1.93 (m, 2H).

後処理

  1. filtrationThe catalyst was filtered off
  2. washwashed with further methanol
  3. filtrationThe combined filtrated
  4. concentrationwashings were concentrated in vacuo
  5. customto give the crude product, which
  6. customwas purified by flash column chromatography
  7. washElution with 5-10% EtOAc/DCM

出典と根拠

ORDレコード
ord-4e310a0df519445781979b6bdef880cb
出典データセット
uspto-grants-2009_05
特許番号
US07538121B2

反応ノート

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