Hydrochloric Acid → 5-Amino-3,4-dihydronaphthalen-1(2H)-one

HRID 719167ノート

反応式

HRID 719167 の反応式
[CH2:1]1[CH2:11][C:9](=[O:10])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.[NH2:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH2:15][CH2:16][CH2:17][C:18]2=[O:23].N([O-])=O.[Na+].[ClH:28]>O.[Cu]Cl>[NH2:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH2:15][CH2:16][CH2:17][C:18]2=[O:23].[Cl:28][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:3]=1[CH2:2][CH2:1][CH2:11][C:9]2=[O:10]

参加物

8

反応物 4

HCID 313Hydrochloric Acid2 回HCID 107241-TetraloneHCID 115065055-Amino-3,4-dihydronaphthalen-1(2H)-oneHCID 23668193Sodium Nitrite

生成物 2

HCID 115065055-Amino-3,4-dihydronaphthalen-1(2H)-oneHCID 122065225-CHLORO-1-TETRALONE

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

5-Amino-1-tetralone was prepared from α-tetralone according to the literature (J. Am. Chem. Soc. 1994, p4852). A mixture of 5-amino-1-tetralone (80 mg) and concentrated hydrochloric acid (1 mL) was cooled to 0° C. A solution of sodium nitrite (35 mg) in water (0.5 mL) was added dropwise to the stirring solution. The cold diazonium solution was then poured rapidly onto a stirring solution of copper (I) chloride (62 mg) in concentrated hydrochloric acid (1 mL). The reaction mixture was allowed to warn to ambient temperature and then stirred for 1.5 hours. The mixture was then extracted with ethyl acetate, washed with water, dried (MgSO4) and the solvent removed in vacuo to yield 5-chloro-1-tetralone as a brown solid (87 mg).

後処理

  1. customto warn to ambient temperature
  2. extractionThe mixture was then extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-1010c3de09b24b38a22df62ec716b90a
出典データセット
uspto-grants-2006_11
特許番号
US07132419B2

反応ノート

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