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

HRID 1733959ノート

反応式

HRID 1733959 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-a842a158e2bc428297bf813c2f75f1e9
出典データセット
uspto-grants-1996_07
特許番号
US05532235

反応ノート

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