3-chloro-1H-indole-4-carbonitrile → HCID 84022392、化合物

HRID 475170ノート

反応式

HRID 475170 の反応式
[Cl:1][C:2]1[C:10]2[C:9]([C:11]#[N:12])=[CH:8][CH:7]=[CH:6][C:5]=2[NH:4][CH:3]=1>N.CO.O.[Ni]>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][NH2:12])[NH:4][CH:3]=1

参加物

6

反応物 1

HCID 866947173-chloro-1H-indole-4-carbonitrile

生成物 1

HCID 84022392HCID 84022392、化合物収率 98.2%

試薬・触媒・溶媒 4

HCID 935Nickel触媒HCID 222Ammonia溶媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a solution of 3-chloro-1H-indole-4-carbonitrile (630.0 mg, 3.57 mmol) in ammonia in MeOH (2M, 45 mL) was added Raney Ni (3.05 g) in water (2 mL). The reaction mixture was then hydrogenated under H2 balloon at 1 atm for 20 h. The reaction mixture was filtered through a pad of Celite®, and the pad was washed alternatively with MeOH (10 mL×3) and water (10 mL×3). Volatile solvents were removed from the filtrate. The remaining crude was extracted with EtOAc (3×75 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. Crystallization from ether/heptane afforded (3-chloro-1H-indol-4-yl)methanamine (133) as a white solid (633 mg, 98.2%). 1H NMR (400 MHz, DMSO) δ 11.33 (br s, 1H), 7.44 (s, 1H), 7.27 (d, J=8.0 Hz, 1H), 7.11-7.01 (m, 2H), 4.18 (s, 2H), 1.73 (br s, 2H).

後処理

  1. customfor 20 h
  2. filtrationThe reaction mixture was filtered through a pad of Celite®
  3. washthe pad was washed alternatively with MeOH (10 mL×3) and water (10 mL×3)
  4. customVolatile solvents were removed from the filtrate
  5. extractionThe remaining crude was extracted with EtOAc (3×75 mL)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customCrystallization from ether/heptane

出典と根拠

ORDレコード
ord-af03cfb4a8b4418bbe8073b75a65e9a7
出典データセット
uspto-grants-2014_01
特許番号
US08637537B2

反応ノート

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