Toluene → HCID 86734038, compound

HRID 1287233Notes

Reaction equation

HRID 1287233 reaction equation
[NH2:1][C:2]1[C:3]([NH:15][CH2:16][CH2:17][CH2:18][CH3:19])=[C:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([CH3:9])=[N:6][C:7]=1[NH2:8].[C:20]1(C)[CH:25]=CC=[CH:22][CH:21]=1>O>[CH2:16]([NH:15][C:3]1[C:2]2[C:7](=[N:8][C:20]([CH3:25])=[C:21]([CH3:22])[N:1]=2)[N:6]=[C:5]([CH3:9])[C:4]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 1140TolueneHCID 123876125,6-Diamino-4-butylamino-2-methylnicotinic acid ethyl ester

Product 1

HCID 86734038HCID 86734038, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

26.6 g. of 5,6-Diamino-4-butylamino-2-methylpyridine-3-carboxylic acid, ethyl ester (0.1 Mol) are dissolved in 150 ml. of toluene. 9 g. of diacetyl are added and the mixture is refluxed while the water formed is removed by a water separator. After about 5 hours, the theoretical amount of water is separated and the solution is evaporated to dryness. The dark oily residue is extracted twice with 100 ml. portions of gasoline and addition of activated charcoal. The gasoline extracts are combined and concentrated to about 100 ml. 8-Butylamino-2,3,6-trimethylprido[2,3-b]pyrazine-7-carboxylic acid, ethyl ester crystallizes on cooling, yield 21 g. (66%); m.p. 97°-99°.

Workup

  1. additionof diacetyl are added
  2. customformed
  3. customis removed by a water separator
  4. customthe theoretical amount of water is separated
  5. customthe solution is evaporated to dryness
  6. extractionThe dark oily residue is extracted twice with 100 ml
  7. additionportions of gasoline and addition of activated charcoal
  8. concentrationconcentrated to about 100 ml
  9. custom8-Butylamino-2,3,6-trimethylprido[2,3-b]pyrazine-7-carboxylic acid, ethyl ester crystallizes
  10. temperatureon cooling

Sources & evidence

ORD record
ord-af9cc9ca4287455c8ebd822f134b0f56
Source dataset
uspto-grants-1976_10
Patent number
US03984412

Reaction notes

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