Pyruvic Acid → 7-chloro-3-methylquinoxalin-2(1h)-one

HRID 1055031Notes

Reaction equation

HRID 1055031 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.O=[C:11]([CH3:15])[C:12](O)=[O:13]>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[NH:8][C:12](=[O:13])[C:11]([CH3:15])=[N:9]2.[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([N:8]=[C:11]([CH3:15])[C:12](=[O:13])[NH:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 1060Pyruvic AcidHCID 72634-Chloro-1,2-diaminobenzene

Product 2

HCID 2581487-chloro-3-methylquinoxalin-2(1h)-oneYield 148.1%HCID 11636992HCID 11636992, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

4-chlorobenzene-1,2-diamine (5 g, 35.1 mmol, Eq: 1.00) was stirred in water (50 ml) at room temperature. 2-Oxopropanoic acid (3.09 g, 2.44 ml, 35.1 mmol, Eq: 1.00) in water (20 ml) was added drop wise. The dark mixture was stirred at room temperature for 30 min. The precipitate was filtered off and washed with water and dried under high vacuum to give 6-chloro-3-methyl-1H-quinoxalin-2-one with 7-chloro-3-methyl-1H-quinoxalin-2-one (5.06 g, 37.1%) as brown solid. MS: m/z=195.03 (M+H+)

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-0fca87ee4d614167b080439c3007499c
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

Loading…