Hydrochloric Acid → Ethyl 4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylate hydrochloride

HRID 553422Notes

Reaction equation

HRID 553422 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH2:11][N:12](C(=O)C)[CH2:13][CH2:14][C:9]=2[O:8][N:7]=1)=[O:5])[CH3:2].[ClH:18]>CCO.O>[ClH:18].[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH2:11][NH:12][CH2:13][CH2:14][C:9]=2[O:8][N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57618621HCID 57618621, compound

Product 1

HCID 44558550Ethyl 4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylate hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

31.1 g (130 mmol) of 5-acetyl-4,5,6,7-tetrahydro-isoxazolo[4,5-c]pyridine-3-carboxylic acid ethyl ester (C) were dissolved in 30 mL of EtOH and combined at RT with 30 mL (260 mmol) of 32% (weight percent) hydrochloric acid solution in water. After two hours' heating with refluxing, the solution was evaporated and introduced into 500 mL of cooled EtOAc (ice bath). The resultant precipitate was separated and dried under a vacuum. 8.13 g (27% of theoretical) of the desired product 4,5,6,7-tetrahydro-isoxazolo[4,5-c]pyridine-3-carboxylic acid ethyl ester hydrochloride (D) were obtained.

Workup

  1. temperatureAfter two hours' heating
  2. temperaturewith refluxing
  3. customthe solution was evaporated
  4. additionintroduced into 500 mL of cooled EtOAc (ice bath)
  5. customThe resultant precipitate was separated
  6. customdried under a vacuum

Sources & evidence

ORD record
ord-d18185d92fac4f97aaa97e7c814821a5
Source dataset
uspto-grants-2011_11
Patent number
US08048879B2

Reaction notes

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