1-(o-Aminophenyl)-4-chloro-1-butanone hydrochloride → 3-(2-Chloroethyl)-4-oxo-(1H)-cinnoline

HRID 704566

Reaction equation

HRID 704566 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:14])[CH2:10][CH2:11][CH2:12][Cl:13].[N:15]([O-])=O.[Na+]>Cl.O>[Cl:13][CH2:12][CH2:11][C:10]1[C:9](=[O:14])[C:4]2[C:3](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:2][N:15]=1

Participants

5

Reactant 2

HCID 232932461-(o-Aminophenyl)-4-chloro-1-butanone hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 200727583-(2-Chloroethyl)-4-oxo-(1H)-cinnoline

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 1-(2-aminophenyl)-4-chlorobutan-1-one hydrochloride (b 11.3 g, 0.0427 mol) in concentrated hydrochloric acid (1200 ml) was cooled down to 0° with stirring. Then sodium nitrite (3.54 g, 0.051mol) in water (25 ml) was added dropwise. On completion of the addition, the reaction mixture was allowed to warm to room temperature and stirred overnight. The solution was evaporated under reduced pressure to dryness. The solid obtained was washed with a solution of sodium acetate and collected by filtration to give the title compound, 5.32 g. Recrystallization from methanol gave the product, m.p. 201-203°.

Workup

  1. additionOn completion of the addition
  2. stirringstirred overnight
  3. customThe solution was evaporated under reduced pressure to dryness
  4. customThe solid obtained
  5. washwas washed with a solution of sodium acetate
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-eb0648a2166841f8bb65d587ff7953ac
Source dataset
uspto-grants-1991_01
Patent number
US04988695

Linked notes

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