Hydrochloric Acid → HCID 178418540, compound

HRID 3867Notes

Reaction equation

HRID 3867 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[N:21]=[C:15]2[NH:16][C:17](=[O:20])[CH2:18][CH:19]=[C:14]2[N:13]=1.[H][H].[ClH:25].O>CN(C)C=O.[Pd]>[ClH:25].[CH3:1][N:2]([CH3:22])[C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[C:12]1[N:21]=[C:15]2[NH:16][C:17](=[O:20])[CH2:18][CH:19]=[C:14]2[N:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 178418361HCID 178418361, compoundHCID 178418554HCID 178418554, compound

Product 1

HCID 178418540HCID 178418540, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

An amount of 1.7 gm of 2-(2-dimethylamino-4-nitro-phenyl)-4H-imidazo[4,5-b]pyridin-5-one is dissolved in 20 ml of dimethylformamide and mixed with 0.2 gm of 10% palladium/charcoal. The mixture is hydrogenated for three hours with hydrogen at ambient temperature under 5 bars of pressure. The mixture is filtered off from the catalyst, the mother liquor is mixed with 100 ml each of ether and of ethyl acetate, and finally 3 ml of etheral hydrochloric acid are added. The precipitate is recrystallized from methanol. After drying over phosphorus pentoxide and potassium hydroxide, a product is obtained which contains 1.5 mol of hydrochloric acid and 0.5 mol of water to 1 mol of base.

Workup

  1. filtrationThe mixture is filtered off from the catalyst
  2. additionthe mother liquor is mixed with 100 ml each of ether and of ethyl acetate, and finally 3 ml of etheral hydrochloric acid
  3. additionare added
  4. customThe precipitate is recrystallized from methanol
  5. dry with materialAfter drying over phosphorus pentoxide and potassium hydroxide
  6. customa product is obtained which

Sources & evidence

ORD record
ord-9bb33ecc109041f0a8377bc723501737
Source dataset
uspto-grants-1988_02
Patent number
US04722929

Reaction notes

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