Hydrochloric Acid → HCID 57142821, compound

HRID 1609581Notes

Reaction equation

HRID 1609581 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:5].Cl.[N:20]([O-])=O.[Na+].[OH-].[Na+]>C(Cl)(Cl)Cl.O>[Br:18][C:15]1[CH:16]=[CH:17][C:2]2[N:1]=[N:20][N:6]([CH2:7][C:8]3[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=3)[C:4](=[O:5])[C:3]=2[CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20081998HCID 20081998, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 57142821HCID 57142821, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6212ChloroformSolvent

Procedure

To a mixture of 29.4 g of 2-amino-5-bromo-N-(3-pyridylmethyl)benzamide, 32 ml of conc. hydrochloric acid and 400 ml of water was dropwise added a solution of 6.83 g and 400 ml of water was dropwise added a solution of 6.83 g of sodium nitrite and 48 ml of water at 0° to 2° C. The resultant mixture was stirred at 0° to 2° C. for 45 minutes, neutralized with 1N aqueous sodium hydroxide and shaken with chloroform. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give 25.6 g of the titled compound.

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a16d9d37a3b14efa8e4ddb9bdc4cf9da
Source dataset
uspto-grants-1995_03
Patent number
US05401756

Reaction notes

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