Hydrochloric Acid → HCID 10220475, compound

HRID 1003419Notes

Reaction equation

HRID 1003419 reaction equation
[N+:1]([C:4]1[C:5](=[O:20])[NH:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:17][CH2:18][CH3:19])=[CH:8][CH:9]=1)([O-])=O.[OH-].[Na+].[H][H].Cl>C(O)C.O.[Pd]>[NH2:1][C:4]1[C:5](=[O:20])[NH:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:17][CH2:18][CH3:19])=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9881998HCID 9881998, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10220475HCID 10220475, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-nitro-6-(2-propoxyphenyl)-2(1H)-pyridinone (0.3 g) in a mixture of ethanol (20 ml) and water (10 ml) containing 2 Normal sodium hydroxide (0.75 ml) was shaken with 10% palladium on charcoal (0.05 g) under hydrogen at atmospheric pressure until the uptake of hydrogen had ceased. The filtered solution was treated with dilute hydrochloric acid to pH 6 and evaporated to half its volume. Water (5 ml) was added and the mixture was filtered to give a crude product, 0.29 g, m.p. 158°-161° C. Recrystallization from 50% aqueous ethanol afforded the pure title compound, 0.11 g, m.p. 164.5°-165.5° C.

Workup

  1. customevaporated to half its volume
  2. additionWater (5 ml) was added
  3. filtrationthe mixture was filtered
  4. customto give a crude product, 0.29 g, m.p. 158°-161° C
  5. customRecrystallization from 50% aqueous ethanol

Sources & evidence

ORD record
ord-f884389e4b654ef2947f64881d2c0b6e
Source dataset
uspto-grants-2000_04
Patent number
US06046216

Reaction notes

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