4-Aminopyridine → HCID 20380322, compound

HRID 1448599Notes

Reaction equation

HRID 1448599 reaction equation
C(O)(=O)[C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)O.[NH2:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[C:10]1([CH:2]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:18][C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 17274-AminopyridineHCID 6463Benzilic acid

Product 1

HCID 20380322HCID 20380322, compoundYield 10.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
220 °C

Procedure

A mixture of 11.4 grams (0.05 mole) of benzilic acid and 4.7 grams (0.05 mole) of 4-aminopyridine was heated at 220° C. for 3.5 hours. After cooling the mixture was dissolved in toluene and washed with 10% sodium carbonate solution and with 2 N hydrochloric acid. The acidic extracts were basified with 5 N sodium hydroxide and the resulting oil extracted into toluene. After drying over magnesium sulphate, the toluene was removed and the yellow oil was recrystallised from light petroleum (b.p. 80°-100° C.) giving 1.35 grams (10% yield) of the title compound, m.p. 152° to 154° C.

Workup

  1. temperatureAfter cooling the mixture
  2. washwashed with 10% sodium carbonate solution and with 2 N hydrochloric acid
  3. extractionthe resulting oil extracted into toluene
  4. dry with materialAfter drying over magnesium sulphate
  5. customthe toluene was removed
  6. customthe yellow oil was recrystallised from light petroleum (b.p. 80°-100° C.)

Sources & evidence

ORD record
ord-8437ab2591bc465faf0701f23e42172f
Source dataset
uspto-grants-1979_12
Patent number
US04180670

Reaction notes

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