Butylamine → 4-Amino-6-butylamino-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester

HRID 2397570Notes

Reaction equation

HRID 2397570 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:17])=[N:8][C:9](Cl)=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[NH2:12])=[O:5])[CH3:2].[CH2:18]([NH2:22])[CH2:19][CH2:20][CH3:21]>C(N(CC)CC)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:17])=[N:8][C:9]([NH:22][CH2:18][CH2:19][CH2:20][CH3:21])=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[NH2:12])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 544502124-Amino-6-chloro-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester

Product 1

HCID 543263044-Amino-6-butylamino-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

26 g. of 4-amino-6-chloro-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester (0.1 mol.) in 300 ml. of alcohol and 15 g. of triethylamine are treated with 7.3 g. of butylamine for 30 minutes at reflux temperature. After this time, the solution is evaporated to dryness and 100 ml. of ethyl acetate are added to the residue. The triethylammonium chloride is filtered off, the solvent is evaporated and the remaining oil recrystallized from methanol. The yield of 4-amino-6-butylamino-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester is 25 g. (84%), m.p. 74°-76° (methanol).

Workup

  1. customAfter this time, the solution is evaporated to dryness and 100 ml
  2. additionof ethyl acetate are added to the residue
  3. filtrationThe triethylammonium chloride is filtered off
  4. customthe solvent is evaporated
  5. customthe remaining oil recrystallized from methanol

Sources & evidence

ORD record
ord-dcade98641cc43ca924329af5d25183e
Source dataset
uspto-grants-1977_05
Patent number
US04022779

Reaction notes

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