Hydrochloric Acid → HCID 70632583, compound

HRID 1415324Notes

Reaction equation

HRID 1415324 reaction equation
N([O-])=O.[Na+].N[CH:6]1[CH:12]([CH2:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[ClH:22]>O.[Cu]Cl>[Cl:22][CH:6]1[CH:12]([CH2:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 23668193Sodium NitriteHCID 70632612HCID 70632612, compound

Product 1

HCID 70632583HCID 70632583, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5 g of sodium nitrite in 20 ml of water is slowly added dropwise at 0° C, whilst stirring, to a solution of 11 g of crude 3-amino-4-cycloheptyl-acetophenone in 70 ml of concentrated hydrochloric acid. After completion of the addition the mixture is stirred for a further 30 minutes at 0° C. The reaction solution is then added dropwise at 0° to 5° C, whilst stirring, to a solution of 7 g of freshly prepared copper-(I) chloride in 30 ml of concentrated hydrochloric acid. After completion of the addition, the mixture is stirred for a further hour at room temperature and a further hour at 40° to 50° C. The reaction mixture is now extracted three times with 200 ml of ether at a time. The organic phases are successively washed with water, 2 N sodium hydroxide solution and again with water, dried over sodium sulphate and evaporated in vacuo. Distillation of the evaporation residue in a high vacuum yields crude 3-chloro-4-cycloheptyl-acetophenone in the fraction boiling at about 130° C/0.05 mm Hg.

Workup

  1. additionAfter completion of the addition the mixture
  2. additionThe reaction solution is then added dropwise at 0° to 5° C
  3. additionAfter completion of the addition
  4. stirringthe mixture is stirred for a further hour at room temperature and a further hour at 40° to 50° C
  5. extractionThe reaction mixture is now extracted three times with 200 ml of ether at a time
  6. washThe organic phases are successively washed with water, 2 N sodium hydroxide solution and again with water
  7. dry with materialdried over sodium sulphate
  8. customevaporated in vacuo
  9. distillationDistillation of the evaporation residue in a high vacuum

Sources & evidence

ORD record
ord-78e57c34b0594ac9a8f3073b23113635
Source dataset
uspto-grants-1977_01
Patent number
US04004026

Reaction notes

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