Water → 3-Hydroxymethyl-6-methyl-2-(3-nitrophenylamino)pyridine

HRID 478722Notes

Reaction equation

HRID 478722 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[N:6][C:5]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1.[BH4-].[K+].[Cl-].[Li+].O>C1COCC1>[OH:2][CH2:3][C:4]1[C:5]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)=[N:6][C:7]([CH3:10])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 433294Lithium ChlorideHCID 4192641Potassium borohydride2×HCID 698496966-Methyl-2-(3-nitrophenylamino)nicotinic acid methyl ester

Product 1

HCID 180026193-Hydroxymethyl-6-methyl-2-(3-nitrophenylamino)pyridineYield 88.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-methyl-2-(3-nitrophenylamino)nicotinic acid methyl ester (13.84 g, 48.18 mmol) in THF (180 ml) was added potassium borohydride (3.12 g, 57.82 mmol) and lithium chloride (2.45 g, 58.82 mmol) and the mixture was heated under reflux. Potassium borohydride (0.52 g, 9.64 mmol) was added three times at one hour intervals and the mixture was further heated under reflux for 1 hour. Evaporation of the solvent under reduced pressure gave a residue which was admixed with water to form crystals. The crystals were collected by filtration, washed successively with water and isopropanol, and dried to give 3-hydroxymethyl-6-methyl-2-(3-nitrophenylamino)-pyridine (11.05 g, 88%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. temperaturethe mixture was further heated
  4. temperatureunder reflux for 1 hour
  5. customEvaporation of the solvent under reduced pressure
  6. customgave a residue which
  7. customto form crystals
  8. filtrationThe crystals were collected by filtration
  9. washwashed successively with water and isopropanol
  10. customdried

Sources & evidence

ORD record
ord-16615466c1ee47b4b6b856d17d26c049
Source dataset
uspto-grants-2003_11
Patent number
US06642250B2

Reaction notes

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