Hydroxyamine hydrochloride → 3-Amino-6-methoxy-5-trifluoromethyl-pyridine-2-carboxylic acid

HRID 887861Notes

Reaction equation

HRID 887861 reaction equation
CC1[N:3]([C:8]2[C:9]([C:20]([OH:22])=[O:21])=[N:10][C:11]([O:18][CH3:19])=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=2)C(C)=CC=1.Cl.NO>CCO.O.CCOC(C)=O>[NH2:3][C:8]1[C:9]([C:20]([OH:22])=[O:21])=[N:10][C:11]([O:18][CH3:19])=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=1

Participants

6

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 58442313HCID 58442313, compound

Product 1

HCID 584423203-Amino-6-methoxy-5-trifluoromethyl-pyridine-2-carboxylic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(2,5-Dimethyl-pyrrol-1-yl)-6-methoxy-5-trifluoromethyl-pyridine-2-carboxylic acid (2.1 g, 6.68 mmol) was dissolved in EtOH (40 ml) and water (20 ml). To this mixture was added TEA (2.79 ml, 20.05 mmol) followed by hydroxylamine hydrochloride (4.64 g, 66.8 mmol). The resulting mixture was heated at reflux for 5 hours. After cooling to RT, the mixture was diluted with EtOAc (100 ml) and washed with aqueous HCl (1M, 100 ml). The aqueous phase was back extracted with EtOAc (100 ml) and the combined organic phases washed with brine (100 ml), dried (MgSO4) and concentrated in vacuo to afford the product as an orange solid. The material can be used crude or recrystallised from isohexane-EtOAc (10:1) LC-MS Rt=1.0 min[M+H]+ 237 (Method 2minLC_v003)

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 5 hours
  3. washwashed with aqueous HCl (1M, 100 ml)
  4. extractionThe aqueous phase was back extracted with EtOAc (100 ml)
  5. washthe combined organic phases washed with brine (100 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4d3ab51b440a46f28c4c533ea5848c91
Source dataset
uspto-grants-2012_08
Patent number
US08247436B2

Reaction notes

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