Nitric Acid → HCID 15636997, compound

HRID 1085476Notes

Reaction equation

HRID 1085476 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][C:9](=[O:11])[NH:10][C:5]2=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[N+:18]([O-])([OH:20])=[O:19]>>[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][C:9](=[O:11])[NH:10][C:5]2=[CH:4][C:3]=1[C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 15636996HCID 15636996, compound

Product 1

HCID 15636997HCID 15636997, compoundYield 97%

Conditions

Temperature
-2 °C

Procedure

1,3-Dihydro-5-methyl-6-phenyl-2H-imidazo[4,5-b]pyridin-2-one (Example 4c, 8.06 g) was added in small portions to 80 ml 90% nitric acid cooled to -2° C. The reaction mixture was stirred at 0° C. for 2 hours and then poured portionwise into ice-water. The solid product was collected, washed with water and ether, and dried in high vacuum at 110°-130° C. to give 9.3 g (97%) of 1,3-dihydro-5-methyl-6-(4-nitrophenyl)-2H-imidazo[4,5-b]pyridin-2-one, m.p. above 300° C. Further purification was accomplished by repeated recrystallization from aqueous dimethylformamide.

Workup

  1. customThe solid product was collected
  2. washwashed with water and ether
  3. customdried in high vacuum at 110°-130° C.

Sources & evidence

ORD record
ord-31693d9ff9af4ae1a56cb6a7d866c18f
Source dataset
uspto-grants-1991_04
Patent number
US05010086

Reaction notes

Loading…