Trifluoroacetic acid → 4-Amino-3-pyridinol N,N-dimethylcarbamate trifluoroacetate

HRID 362209Notes

Reaction equation

HRID 362209 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]([O:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[N:12]=CN(C)C)=[O:4].[F:18][C:19]([F:24])([F:23])[C:20]([OH:22])=[O:21]>O>[F:18][C:19]([F:24])([F:23])[C:20]([OH:22])=[O:21].[CH3:1][N:2]([CH3:17])[C:3](=[O:4])[OH:5].[NH2:12][C:11]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[OH:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 538347434-[[(Dimethylamino)methylene]amino]-3-pyridinol N,N-dimethylcarbamate

Product 1

HCID 675680254-Amino-3-pyridinol N,N-dimethylcarbamate trifluoroacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture prepared from 4-[[(dimethylamino)methylene]amino]-3-pyridinol N,N-dimethylcarbamate (7.4 g), trifluoroacetic acid (30 mL) and water (15 mL) was refluxed for a half hour. The reaction mixture was concentrated, filtered over a pad of basic alumina (CH2Cl2, 30% ethyl acetate/CH2Cl2, ethyl acetate), recrystallized from methano/diethyl ether, and dried under high vacuum and refluxing ethanol to yield 4.97 g of microcrystals, m.p. 159°-160° C.

Workup

  1. temperaturewas refluxed for a half hour
  2. concentrationThe reaction mixture was concentrated
  3. filtrationfiltered over a pad of basic alumina (CH2Cl2, 30% ethyl acetate/CH2Cl2, ethyl acetate)
  4. customrecrystallized from methano/diethyl ether
  5. customdried under high vacuum
  6. temperaturerefluxing ethanol
  7. customto yield 4.97 g of microcrystals, m.p. 159°-160° C.

Sources & evidence

ORD record
ord-8c45545cee2d4e0ca96ca139e6295b3b
Source dataset
uspto-grants-1999_02
Patent number
US05869480

Reaction notes

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