Hydrochloric Acid → HCID 13336722, compound

HRID 1906187Notes

Reaction equation

HRID 1906187 reaction equation
C(O[CH:9]1[C:14](=[O:15])[CH:13]=[C:12](OCC2C=CC=CC=2)[N:11]=[CH:10]1)C1C=CC=CC=1.Cl.[CH3:25]N.Cl.[CH2:28]([OH:30])C>>[OH:30][CH2:28][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH3:25])[CH:10]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6364545Methylamine hydrochlorideHCID 70275106HCID 70275106, compound

Product 1

HCID 13336722HCID 13336722, compoundYield 15%

Procedure

3-Benzyloxy-6-benzyloxypyrid-4-one (5.0 g) and methylamine hydrochloride (1.56 g) are dissolved in aqueous ethanol (300 ml of 2:1 H2O-C2H5OH by volume containing 2 g of sodium hydroxide). The reaction mixture is stirred at room temperature for 6 days and then acidified with concentrated HCl to pH 2.0. The yellow mixture is evaporated to dryness and the resulting solid residue is heated under reflux with concentrated HCl (50 ml) for 30 minutes. The product is rotary evaporated to dryness yielding a brown residue which on trituration with acetone forms crystals. Recrystallisation of these from ethanol gives 3-hydroxymethyl-1-methylpyrid-4-one in 15% yield, m.p. 185°-186° C.; δ(d6DMSO), 3.9 (s, 3H), 4.6 (s, 2H), 7.4 (s, 1H), 8.3 (s, 1H).

Workup

  1. customThe yellow mixture is evaporated to dryness
  2. temperaturethe resulting solid residue is heated
  3. temperatureunder reflux with concentrated HCl (50 ml) for 30 minutes
  4. customThe product is rotary evaporated to dryness
  5. customyielding a brown residue which on trituration with acetone forms crystals
  6. customRecrystallisation of these from ethanol

Sources & evidence

ORD record
ord-0862120ac015425495dbe6c3180a0303
Source dataset
uspto-grants-1987_03
Patent number
US04650793

Reaction notes

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