Ethanol → 6-Chloro-4-[[3-(dimethylamino)propyl]amino]-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester

HRID 1973105Notes

Reaction equation

HRID 1973105 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:17])=[N:8][C:9]([Cl:16])=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1Cl)=[O:5])[CH3:2].C(O)C.[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25][NH2:26]>C(N(CC)CC)C>[Cl:16][C:9]1[N:8]=[C:7]([CH3:17])[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:11]([NH:26][CH2:25][CH2:24][CH2:23][N:22]([CH3:27])[CH3:21])[C:10]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 12387594Ethyl 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

139.5 g. of 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester (0.5 Mol.) in 500 ml. of ethyl alcohol are heated at reflux temperature. 60 g. of triethylamine are added and then 51 g. of 3-(dimethylamino)propylamine are slowly dropped in with stirring. After the addition is completed, heating is continued for 10 minutes. The solvent is distilled off and the residue is treated with 200 ml. of water and made alkaline (pH 9-10) with sodium hydroxide. The mixture is extracted three times with 150 ml. portions of ether. The organic layers are combined, dried over calcium chloride and evaporated to dryness. The residue is recrystallized from methanol, yield 110 g. (64%), m.p. < 20°.

Workup

  1. temperatureat reflux temperature
  2. additionAfter the addition
  3. temperatureheating
  4. distillationThe solvent is distilled off
  5. additionthe residue is treated with 200 ml
  6. extractionThe mixture is extracted three times with 150 ml
  7. dry with materialdried over calcium chloride
  8. customevaporated to dryness
  9. customThe residue is recrystallized from methanol, yield 110 g

Sources & evidence

ORD record
ord-a5d7ece29f2c49df909d384366c8f97c
Source dataset
uspto-grants-1976_12
Patent number
US03996233

Reaction notes

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