Hydrochloric Acid → HCID 67188193, compound

HRID 735858Notes

Reaction equation

HRID 735858 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:13])[C:10]=1[CH2:11][NH2:12])[C:5](N)=[O:6].[OH-:14].[Na+].Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([OH:14])=[O:6])[CH:8]=[C:9]([Br:13])[C:10]=1[CH2:11][NH2:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67187225HCID 67187225, compound

Product 1

HCID 67188193HCID 67188193, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3,5-dibromo-4-aminomethyl benzamide (40 g, 0.129 mol), methanol (500 mL) and an aqueous solution of NaOH (10%, 310 mL) was refluxed for 20 h. The reaction mixture was concentrated to 150 mL and cooled to 0° C. The solid precipitate obtained was filtered, washed with diethyl ether (500 mL). The solid obtained was acidified with an aqueous solution of HCl (1.5 N, 100 mL) to pH=6 to give solid precipitate. The solid was filtered, washed with water and dried under vacuum to give 2,6-dibromo-4-carboxy benzylamine (35 g, 87%) as a solid.

Workup

  1. concentrationThe reaction mixture was concentrated to 150 mL
  2. customThe solid precipitate obtained
  3. filtrationwas filtered
  4. washwashed with diethyl ether (500 mL)
  5. customThe solid obtained
  6. customto give solid precipitate
  7. filtrationThe solid was filtered
  8. washwashed with water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-e7c9caec6654480ab6e6eb7d3ba86471
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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