Water → (2-Chloro-4-nitrophenyl)(6,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepin-5-yl)methanone

HRID 863011ノート

反応式

HRID 863011 の反応式
[N:1]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:19][C:20]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23].O>ClCCl>[Cl:19][C:20]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[CH:25][C:21]=1[C:22]([N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]1=2)=[O:23]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 81522Benzoyl chloride, 2-chloro-4-nitro-HCID 124131726,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepine

生成物 1

HCID 19699064(2-Chloro-4-nitrophenyl)(6,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepin-5-yl)methanone収率 67.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a mixture of 2.90 g of 6,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepine, 2.37 g of triethylamine in 40 ml of dichloromethane is added 5.16 g of 2-chloro-4-nitrobenzoyl chloride in 50 ml of dichloromethane. The mixture is stirred at room temperature under argon for 3 hours and then poured into water. The organic layer is separated and washed with 1N NaHCO3, H2O, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate, the pad washed with CH2Cl2 and ethyl acetate and the filtrate concentrated to dryness. The residual solid (7.13 g) is triturated with ethyl acetate to give 4.41 g of off-white crystals, m.p. 143°-145° C.

後処理

  1. customThe organic layer is separated
  2. washwashed with 1N NaHCO3, H2O, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  5. washthe pad washed with CH2Cl2 and ethyl acetate
  6. concentrationthe filtrate concentrated to dryness
  7. customThe residual solid (7.13 g) is triturated with ethyl acetate

出典と根拠

ORDレコード
ord-c6ac7e9c14e847589d2fd70a1e383f73
出典データセット
uspto-grants-1998_02
特許番号
US05719278

反応ノート

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