Hydrochloric Acid → HCID 13369386, compound

HRID 443395Notes

Reaction equation

HRID 443395 reaction equation
Br[CH:2]1[C:7]2=[N:8][CH:9]=[C:10]([C:13]([OH:15])=[O:14])[C:11](=[O:12])[N:6]2[CH:5]([CH3:16])[CH2:4][CH2:3]1.C(Cl)(Cl)Cl.[CH2:21]([NH2:25])[CH2:22][CH2:23][CH3:24].Cl>O>[CH2:21]([NH:25][C:2]1[C:7]2=[N:8][CH:9]=[C:10]([C:13]([OH:15])=[O:14])[C:11](=[O:12])[N:6]2[CH:5]([CH3:16])[CH2:4][CH:3]=1)[CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 8007ButylamineHCID 15584879HCID 15584879, compound

Product 1

HCID 13369386HCID 13369386, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

14.35 g. (0.05 mole) of 9-bromo-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid are dissolved in 100 ml. of anhydrous chloroform. To the solution 15.0 ml. (0.15 mole) of n-butyl amine are added. The reaction mixture is allowed to stand for 3 days at room temperature, whereafter 70 ml. of water are added. The pH-value of the aqueous layer is adjusted under vigorous stirring to 2 by adding 10% by W/V hydrochloric acid solution. The organic layer is separated and the aqueous layer is shaken out with 2×50 ml. of chloroform. The combined organic layers are dried above calcinated sodium sulfate, finally the solvent is distilled off at reduced pressure. The residue is crystallized from methanol. 4.3 g. (31%) of 9-(n-butyl-amino)-6-methyl-4-oxo-6,7-dihydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid is obtained. Melting point: 13.5°-137° C.

Workup

  1. customThe organic layer is separated
  2. stirringthe aqueous layer is shaken out with 2×50 ml
  3. customThe combined organic layers are dried
  4. distillationfinally the solvent is distilled off at reduced pressure
  5. customThe residue is crystallized from methanol

Sources & evidence

ORD record
ord-6040558d4dc44f1ea2d0b809dc916d1d
Source dataset
uspto-grants-1981_04
Patent number
US04260612

Reaction notes

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