4-Amino-3-hydroxypyridine → 4-[[(Diisopropylamino)methylene]amino]-3-pyridinol

HRID 362193

Reaction equation

HRID 362193 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[OH:8].CO[CH:11](OC)[N:12]([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14]>C1(C)C=CC=CC=1>[CH:13]([N:12]([CH:11]=[N:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[OH:8])[CH:16]([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 27624194-Amino-3-hydroxypyridineHCID 13161384Diisopropylformamide Dimethylacetal (>90%)

Product 1

HCID 153809314-[[(Diisopropylamino)methylene]amino]-3-pyridinol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-amino-3-pyridinol (3.0 g), N,N-diisopropylformamide dimethyl acetal (9.54 g) and 15 ml dry toluene was stirred at room temperature for 18 hours and thereafter heated to 60°-70° C. After 90 minutes, the mixture was cooled to room temperature, concentrated in vacuo and chromatographed on silica using 10:90 CH3OH/ethyl acetate as an eluent. The fractions containing the desired product were combined and concentrated to a thick oil, which solidified on refrigeration. This solid (5.3 g) was triturated with hexane three times to provide the product as a white solid, m.p. 77°-79° C.

Workup

  1. temperatureheated to 60°-70° C
  2. waitAfter 90 minutes
  3. temperaturethe mixture was cooled to room temperature
  4. concentrationconcentrated in vacuo
  5. customchromatographed on silica using 10:90 CH3OH/ethyl acetate as an eluent
  6. additionThe fractions containing the desired product
  7. concentrationconcentrated to a thick oil, which
  8. customThis solid (5.3 g) was triturated with hexane three times

Sources & evidence

ORD record
ord-ee331e0211f14d84a9a360bd9641a669
Source dataset
uspto-grants-1999_02
Patent number
US05869480

Linked notes

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