Aniline → HCID 13369414, compound

HRID 443400Notes

Reaction equation

HRID 443400 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(#N)C.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O>[NH:20]([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:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 6342AcetonitrileHCID 15584879HCID 15584879, compound

Product 1

HCID 13369414HCID 13369414, compoundYield 86.11%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

148.7 g. (0.50 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 250 ml. of acetonitrile and 100 ml. of aniline are further added. The solution is stirred for 2 days in a nitrogen gas atmosphere at room temperature. 1000 ml. of water is added and the mixture is stirred for a further half an hour. The crystals are filtered and washed with water and finally reboiled in 1400 ml. of methanol. 128.8 g. (86.11%) of 9-anilino-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid are obtained. Melting point: 198°-199° C.

Workup

  1. stirringthe mixture is stirred for a further half an hour
  2. filtrationThe crystals are filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-bd461e68b4a545d3856109a13b26e4a6
Source dataset
uspto-grants-1981_04
Patent number
US04260612

Reaction notes

Loading…