Hydrochloric Acid → 7-Chloro-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1369010Notes

Reaction equation

HRID 1369010 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][CH2:12][C:13]2=[O:16])=[CH:8][CH:7]=1.[ClH:17]>O.Cl[Cu]>[Cl:17][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][CH2:12][C:13]2=[O:16])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 3271777-Amino-1,2,3,4-tetrahydronaphthalen-1-oneHCID 23668193Sodium Nitrite

Product 1

HCID 2566777-Chloro-1,2,3,4-tetrahydronaphthalen-1-one

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

NaNO2 (0.7 g; 10 mmol) dissolved in water (10 mL) was added with stirring to an ice-cold solution of 7-amino-1-tetralone (1.4 g; 8.8 mmol; from step (i) above) in conc HCl (aq.) over a period of 5 minutes. The resultant cold solution was then added slowly to an ice-cold solution of CuCl (1.5 g, 15 mmol) in conc. HCl (aq.), whereafter the resultant solution was stirred at RT for 2 hours and at 60° C. for 30 minutes. The slurry was cooled with ice, and the resultant precipitate was suction filtered, washed with water, and air dried. Yield 1.50 g (94%).

Workup

  1. additionwas added
  2. temperatureThe slurry was cooled with ice
  3. filtrationfiltered
  4. washwashed with water, and air
  5. customdried

Sources & evidence

ORD record
ord-b36fbb60e4e04a019038a6508006a250
Source dataset
uspto-grants-2003_06
Patent number
US06576657B2

Reaction notes

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