Hydrochloric Acid → 3-(2-Chloroethyl)-8-methyl-4(1H)-cinnolinone

HRID 704570

Reaction equation

HRID 704570 reaction equation
Cl.[NH2:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:10](=[O:15])[CH2:11][CH2:12][CH2:13][Cl:14].Cl.[N:17]([O-])=O.[Na+]>O>[Cl:14][CH2:13][CH2:12][C:11]1[C:10](=[O:15])[C:4]2[C:3](=[C:8]([CH3:9])[CH:7]=[CH:6][CH:5]=2)[NH:2][N:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 200727531-(2-Amino-3-methylphenyl)-4-chlorobutan-1-one hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 200727593-(2-Chloroethyl)-8-methyl-4(1H)-cinnolinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1-(2-amino-3-methylphenyl)-4-chlorobutan-1-one hydrochloride (20 g, 0.081 Mol) and concentrated hydrochloric acid (1000 ml) at 0° was added dropwise a solution of sodium nitrite (6.07 g, 0.088 mol) in water (50 ml) maintaining the temperature below 5°. The reaction mixture was stirred at room temperature for 20 hours. The solvent was evaporated under reduced pressure to give a solid. The solid was washed with sodium acetate solution and collected by filtration and dried, 13.5 g. Recrystallization from methanol gave the title compound, m.p. 222-225°

Workup

  1. temperaturemaintaining the temperature below 5°
  2. customThe solvent was evaporated under reduced pressure
  3. customto give a solid
  4. washThe solid was washed with sodium acetate solution
  5. filtrationcollected by filtration
  6. customdried
  7. customRecrystallization from methanol

Sources & evidence

ORD record
ord-271f26a3f9b64f0ba88bd6086d12c5b6
Source dataset
uspto-grants-1991_01
Patent number
US04988695

Linked notes

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