Ammonia → 7-benzylamino-6,7-dihydro-5H-benzocyclohepten-2-ol

HRID 274058ノート

反応式

HRID 274058 の反応式
N([O-])=[O:2].[Na+].[CH2:5]([NH:12][CH:13]1[CH:19]=[CH:18][C:17]2[CH:20]=[C:21](N)[CH:22]=[CH:23][C:16]=2[CH2:15][CH2:14]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N>S(=O)(=O)(O)O.O>[CH2:5]([NH:12][CH:13]1[CH:19]=[CH:18][C:17]2[CH:20]=[C:21]([OH:2])[CH:22]=[CH:23][C:16]=2[CH2:15][CH2:14]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

6

反応物 3

HCID 222AmmoniaHCID 23191869N7-benzyl-6,7-dihydro-5H-benzocyclohepten-2,7-diamineHCID 23668193Sodium Nitrite

生成物 1

HCID 200947657-benzylamino-6,7-dihydro-5H-benzocyclohepten-2-ol収率 77.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1118Sulfuric Acid溶媒2 回

実験手順

Sodium nitrite (609 mg) aqueous solution (6 ml) was added dropwise to a stirred suspension of N7 -benzyl-6,7-dihydro-5H-benzocycloheptene-2,7-diamine (2.22 g) in 6N sulfuric acid (22 ml) under ice cooling over 15 minutes and the resulting solution was stirred at the same temperature for 30 minutes. The solution was added dropwise to a stirred solution of sulfuric acid (3 ml) in water (15 ml) at 75° C. over 15 minutes. The resulting mixture was stirred at the same temperature for 30 minutes, cooled with ice-water bath, basified with 28% ammonia solution (15 ml), and extracted six times with dichloromethane. The combined extracts were evaporated in vacuo and chromatographed over silica gel using dichloromethane and methanol to afford 7-benzylamino-6,7-dihydro-5H-benzocyclohepten-2-ol (1.72 g) as a pale brown oil.

後処理

  1. stirringThe resulting mixture was stirred at the same temperature for 30 minutes
  2. temperaturecooled with ice-water bath
  3. extractionextracted six times with dichloromethane
  4. customThe combined extracts were evaporated in vacuo
  5. customchromatographed over silica gel

出典と根拠

ORDレコード
ord-1fab16b4d4b0485c9c3a08db36b3902e
出典データセット
uspto-grants-1995_02
特許番号
US05387710

反応ノート

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