Acetic Anhydride → HCID 67263601、化合物

HRID 1688016ノート

反応式

HRID 1688016 の反応式
[C:1](OC(=O)C)(=[O:3])[CH3:2].[N+:8]([C:11]1[CH:12]=[CH:13][C:14]2[O:20][CH2:19][CH2:18][CH2:17][NH:16][C:15]=2[CH:21]=1)([O-:10])=[O:9].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(#N)C.CCOC(C)=O>[N+:8]([C:11]1[CH:12]=[CH:13][C:14]2[O:20][CH2:19][CH2:18][CH2:17][N:16]([C:1](=[O:3])[CH3:2])[C:15]=2[CH:21]=1)([O-:10])=[O:9]

参加物

7

反応物 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 109871302,3,4,5-Tetrahydro-7-nitro-1,5-benzoxazepine

生成物 1

HCID 67263601HCID 67263601、化合物収率 74%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

Acetic anhydride (1.00 mL, 10.6 mmol;) was added to a solution of 2-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (0.580 g, 2.99 mmol), 4-Dimethylaminopyridine (20 mg, 0.1 mmol; Acros) and Triethylamine (1.0 mL, 7.2 mmol) in Acetonitrile (10 mL; Acros). The reaction was stirred under an atmosphere of Nitrogen overnight. Conversion was moderate, so the mixture was heated at 50° C. for the weekend. The solution was conc. in vacuo, diluted with 25 mL EtOAc then washed with 1N HCl (10 mL), satd. sodium bicarbonate (10 mL) and brine (10 mL). After drying over sodium sulfate, the solution was conc. and the residue chromatographed (ISCO, 80 g SiO2, 0-65% EtOAc:Hex) to afford 1-(2-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone as light yellow solids (522 mg, 74%). Mixture of rotamers in 1H-NMR, resulting in very broad signals for the aliphatic methylenes. 13C-NMR (CDCl3): 169.8, 160.3, 142.7, 134.3, 124.8, 124.6, 122.6, 71.1, 45.0, 28.0, 22.4

後処理

  1. washthen washed with 1N HCl (10 mL)
  2. dry with materialAfter drying over sodium sulfate
  3. customthe residue chromatographed (ISCO, 80 g SiO2, 0-65% EtOAc:Hex)

出典と根拠

ORDレコード
ord-b97659a403534ba1b17f898ec1aeac82
出典データセット
uspto-grants-2012_04
特許番号
US08148391B2

反応ノート

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