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

HRID 719167노트

반응식

HRID 719167 반응식
[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]

참가 물질

8

반응물 4

HCID 313Hydrochloric Acid2회HCID 107241-TetraloneHCID 115065055-Amino-3,4-dihydronaphthalen-1(2H)-oneHCID 23668193Sodium Nitrite

생성물 2

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

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1010c3de09b24b38a22df62ec716b90a
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132419B2

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