Ammonia → HCID 19785040, compound

HRID 256516Notes

Reaction equation

HRID 256516 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([CH3:13])=[CH:7][C:8]=2[CH3:12])[N:3]=1.[Br:14]Br.OS([O-])=O.[Na+].N>C(O)(=O)C.O>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([CH3:13])=[C:7]([Br:14])[C:8]=2[CH3:12])[N:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 24408Bromine2×HCID 973655,7-Dimethyl-1,8-naphthyridin-2-ylamineHCID 23665763Sodium Bisulfite

Product 1

HCID 19785040HCID 19785040, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

173 g (1 mol) of 2-amino-5,7-dimethyl-1,8-naphthyridine is suspended in 500 ml of glacial acetic acid. At 60° C. and with stirring, 160 g (1 mol) of bromine is dripped in, the solid going into solution. After all has been added, the mixture is stirred overnight at room temperature (20° C.) and then poured into 1 liter of water. Excess bromine is reduced by adding a small amount of NaHSO3. The pH is brought to 4 with concentrated NH3 solution. The mixture is stirred for about 30 minutes and the precipitate is filtered off and dried under reduced pressure to give 132 g of a pale brown solid.

Workup

  1. additionAfter all has been added
  2. stirringthe mixture is stirred overnight at room temperature (20° C.)
  3. stirringThe mixture is stirred for about 30 minutes
  4. filtrationthe precipitate is filtered off
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-6c64eff2fc5c4746a539935d947e4e05
Source dataset
uspto-grants-1993_11
Patent number
US05258356

Reaction notes

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