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

HRID 719167Notes

Reaction equation

HRID 719167 reaction equation
[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]

Participants

8

Reactant 4

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

Product 2

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

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1010c3de09b24b38a22df62ec716b90a
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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