Methanol → 4-[[3-(Dimethylamino)propyl]amino]-6-ethylamino-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester

HRID 1973106Notes

Reaction equation

HRID 1973106 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:23])=[N:8][C:9](Cl)=[C:10]([N+:19]([O-:21])=[O:20])[C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])=[O:5])[CH3:2].CO.[CH2:26]([NH2:28])[CH3:27]>C(N(CC)CC)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:23])=[N:8][C:9]([NH:28][CH2:26][CH3:27])=[C:10]([N+:19]([O-:21])=[O:20])[C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 6341EthylamineHCID 537171606-Chloro-4-[[3-(dimethylamino)propyl]amino]-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester

Product 1

HCID 538354624-[[3-(Dimethylamino)propyl]amino]-6-ethylamino-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

34.5 g. of 6-chloro-4-[[3-(dimethylamino)propyl]amino]-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester (0.1 Mol.) are dissolved in 200 ml. of methanol. A mixture of 15 g. of triethylamine and 6 g. of ethylamine are added and the solution is refluxed for one hour with stirring. The solvent is distilled off in vacuo and the residue treated with about 100 ml. of water. The aqueous phase is extracted three times with 100 ml. portions of ether, the ether layers are combined, dried over calcium chloride and the solvent distilled off. The resulting yellow oil is recrystallized from ether/ligroin, yield 31 g. (88%), m.p. < 20°.

Workup

  1. additionA mixture of 15 g
  2. temperaturethe solution is refluxed for one hour
  3. distillationThe solvent is distilled off in vacuo
  4. additionthe residue treated with about 100 ml
  5. extractionThe aqueous phase is extracted three times with 100 ml
  6. dry with materialdried over calcium chloride
  7. distillationthe solvent distilled off
  8. customThe resulting yellow oil is recrystallized from ether/ligroin, yield 31 g

Sources & evidence

ORD record
ord-53640852778a4cd6a7fc6c61855287d0
Source dataset
uspto-grants-1976_12
Patent number
US03996233

Reaction notes

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