Hydrochloric Acid → 3-amino-4-hydroxy-1-methylpyridin-2(1H)-one hydrochloride

HRID 575710Notes

Reaction equation

HRID 575710 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([O:8]CC2C=CC=CC=2)=[C:4]([N+:16]([O-])=O)[C:3]1=[O:19].CCO.CN(C=O)C.[ClH:28]>CO.[Pd]>[ClH:28].[NH2:16][C:4]1[C:3](=[O:19])[N:2]([CH3:1])[CH:7]=[CH:6][C:5]=1[OH:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6228DimethylformamideHCID 1180219594-(benzyloxy)-1-methyl-3-nitropyridin-2(1H)-one

Product 1

HCID 1180221633-amino-4-hydroxy-1-methylpyridin-2(1H)-one hydrochlorideYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the title compound of step 2 (2.00 g, 7.69 mmol, 1.00 Eq) in MeOH (50 mL)/EtOH (50 mL)/DMF (10 mL) was added Pd—C (10%, 0.2 g) under N2. The suspension was purged with H2 three times and hydrogenated under a balloon for 5 h. The catalyst was removed by fitration, and anhydrous HCl in methanol (10 mL, 1.25 M) was added. Concentration left a residue which was treated a second time with HCl in methanol. Evaporation of the volatile components and triturtion with DCM (30 mL)/hexane (30 mL) gave the title compound (1.29 g, 7.30 mmol, yield: 95%) as a pink HCl salt after drying. 1H NMR: (DMSO-d6, 400 MHz) δ: 9.45-8.02 (br, 3H), 7.64 (d, J=7.6 Hz, 1H), 3.27 (d, J=7.6 Hz, 1H), 3.43 (s, 3H). LCMS: 163.0 (M+Na)+

Workup

  1. customThe suspension was purged with H2 three times and hydrogenated under a balloon for 5 h
  2. customThe catalyst was removed by fitration, and anhydrous HCl in methanol (10 mL, 1.25 M)
  3. additionwas added
  4. concentrationConcentration
  5. waitleft a residue which
  6. additionwas treated a second time with HCl in methanol
  7. customEvaporation of the volatile components and triturtion with DCM (30 mL)/hexane (30 mL)

Sources & evidence

ORD record
ord-a7deac54ded84023a2f8e3f1ca964753
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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