Hydrochloric Acid → HCID 14822879, compound

HRID 1088674Notes

Reaction equation

HRID 1088674 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][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1.Cl>C(O)C.O>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:3]2[CH:4]=[C:5]3[NH:10][C:9](=[O:11])[NH:8][C:6]3=[N:7][C:2]=2[CH3:1])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15636997HCID 15636997, compound

Product 1

HCID 14822879HCID 14822879, compoundYield 128.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 10.11 g 1,3-dihydro-5-methyl-6-(4-nitrophenyl)-2H-imidazo[4,5-b]pyridin-2-one (Example 5) in 200 ml absolute ethanol and 80 ml water was added 25.34 g stannous chloride dihydrate (SnCl2.2H2O) and 120 ml concentrated hydrochloric acid. The reaction mixture was heated at reflux for 6 hours, then cooled to room temperature and allowed to stand until crystals formed. The latter was collected by decantation and additional product obtained by concentration of the mother liquors to 60% of the original volume. The total solid product was washed with ethanol and ether and dried (high vacuum at 120° C.) to give 11.52 g 6-(4-aminophenyl)-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one in the form of its hydrochloride salt and containing ethanol of crystallization, m.p. 277-283° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 6 hours
  3. customformed
  4. customThe latter was collected by decantation and additional product
  5. customobtained by concentration of the mother liquors to 60% of the original volume
  6. washThe total solid product was washed with ethanol and ether
  7. customdried (high vacuum at 120° C.)

Sources & evidence

ORD record
ord-004f4d3e10074eebba61779e906e9e41
Source dataset
uspto-grants-1990_10
Patent number
US04963561

Reaction notes

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