Ammonia → HCID 55281675, compound

HRID 2055814Notes

Reaction equation

HRID 2055814 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.[NH3:11]>>[NH2:11][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([CH3:10])[N:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 22504306(2-Chloro-6-methylpyridin-4-yl)methanol

Product 1

HCID 55281675HCID 55281675, compound

Conditions

Temperature
210 °C

Procedure

A bomb was charged with 2 (30.0 g, 0.190 mol) and aqueous conc NH3 (225 mL) and the resulting mixture was heated at 210° C. for 20 h. The system was cooled to room temperature, the volatiles removed in vacuo and the residue purified by column chromatography (dichloromethane: 0.4N NH3 in MeOH 9:1) to give (2-amino-6-methyl pyridine-4-yl)-methanol as a mixture of free base and hydrochloride salt. The mixture was redissolved in dichloromethane:i-PrOH 1:1 (1 L) and treated with 20% aqueous NaOH (500 mL). The layers were separated and the organic phase extracted with dichloromethane:i-PrOH 1:1 (1×1 L). The combined organic phase was dried and the solvent evaporated to give (2-amino-6-methyl pyridine-4-yl)-methanol 3 (15.51 g, 59%) as pale orange crystals.

Workup

  1. temperatureThe system was cooled to room temperature
  2. customthe volatiles removed in vacuo
  3. customthe residue purified by column chromatography (dichloromethane: 0.4N NH3 in MeOH 9:1)

Sources & evidence

ORD record
ord-156fc459c12b45eab642809f933324cc
Source dataset
uspto-grants-2008_02
Patent number
US07332604B2

Reaction notes

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