Hydrochloric Acid → HCID 21474457, compound

HRID 2294254Notes

Reaction equation

HRID 2294254 reaction equation
[ClH:1].C([O:9][C:10]1[C:15](=[O:16])[CH:14]=[CH:13][N:12]([CH2:17][CH2:18][OH:19])[C:11]=1[CH:20]([OH:30])[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)C1C=CC=CC=1>C1(C)C=CC=CC=1>[ClH:1].[OH:9][C:10]1[C:15](=[O:16])[CH:14]=[CH:13][N:12]([CH2:17][CH2:18][OH:19])[C:11]=1[CH:20]([OH:30])[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21474319HCID 21474319, compound

Product 1

HCID 21474457HCID 21474457, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

1.9 ml of 37% conc. HCl are poured over 0.19 g of 3-benzyloxy-1-(2-hydroxy-ethyl)-2-[hydroxy-(4-nitro-phenyl)-methyl]-1H-pyridin-4-one. The mixture is heated with stirring at 100° C. for 45 minutes. 20 ml of toluene are added and distillation is carried out at a bath temperature of 50° C. and under a pressure of 60 mbar using a rotary evaporator. The addition of toluene and the distillation are repeated four times. The crystalline residue is recrystallised from ethanol, yielding 3-hydroxy-1-(2-hydroxy-ethyl)-2-[hydroxy-(4-nitro-phenyl)-methyl]-1H-pyridin-4-one hydrochloride. Brown crystals, m.p.: from 204° C. with decomposition.

Workup

  1. temperatureThe mixture is heated
  2. distillationdistillation
  3. customis carried out at a bath
  4. customtemperature of 50° C.
  5. customa rotary evaporator
  6. additionThe addition of toluene
  7. distillationthe distillation
  8. customThe crystalline residue is recrystallised from ethanol

Sources & evidence

ORD record
ord-d10d7ff4e532490da3ccd6fda3ef6e59
Source dataset
uspto-grants-1997_11
Patent number
US05688815

Reaction notes

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