Methoxyacetyl chloride → 2-Methoxy-1-(3-nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone

HRID 1041702ノート

反応式

HRID 1041702 の反応式
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=1)([O-:3])=[O:2].[CH3:15][O:16][CH2:17][C:18](Cl)=[O:19]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:15][O:16][CH2:17][C:18]([N:8]1[C:7]2[CH:13]=[CH:14][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[O:12][CH2:11][CH2:10][CH2:9]1)=[O:19]

参加物

5

反応物 2

HCID 96623Methoxyacetyl chlorideHCID 672641803-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene

生成物 1

HCID 672634692-Methoxy-1-(3-nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

実験手順

3-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (203 mg, 1.04 mmol) and 4-Dimethylaminopyridine (13 mg, 0.10 mmol) in Pyridine (3.5 mL) was treated with Methoxyacetyl chloride (0.15 mL, 1.6 mmol) was added to the vial and stirred at rt. After 4 h, the mixture was partitioned between EtOAc and water, separated and the org. layer was washed with 1N HCl. After washing with brine and drying, 2-Methoxy-1-(3-nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone was isolated following silica gel chromatography (0-100% EtOAc:Hex) as yellow solids (270 mg, 97%). 1H-NMR (CDCl3): 7.96 (m, 2H), 7.36 (m, 1H), 4.82 (m, 1H), 4.25 (m, 2H), 3.89 (m, 3H), 3.34 (s, 3H), 2.96 (m, 1H), 2.13 (m, 2H).

後処理

  1. additionwas added to the vial and
  2. customthe mixture was partitioned between EtOAc and water
  3. customseparated
  4. washlayer was washed with 1N HCl
  5. washAfter washing with brine
  6. customdrying

出典と根拠

ORDレコード
ord-3b2a8b26d2fc4f1381b05c45a8e1fb79
出典データセット
uspto-grants-2013_10
特許番号
US08552186B2

反応ノート

読み込み中…