Hydrochloric Acid → 2-Chloro-6-methylamino-benzoic acid

HRID 1760742Notes

Reaction equation

HRID 1760742 reaction equation
[Na].[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([NH2:12])[C:8]=1[C:9]([OH:11])=[O:10].[CH2:13]=O.[BH4-].[Na+].[OH-].[K+].Cl>CO>[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([NH:12][CH3:13])[C:8]=1[C:9]([OH:11])=[O:10]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 750712-Amino-6-chlorobenzoic acidHCID 4311764Sodium borohydrideHCID 5360545Sodium

Product 1

HCID 627107682-Chloro-6-methylamino-benzoic acidYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium (3.35 g, 146 mmol) was slowly added to stirred MeOH (45 mL). Upon completion of gas evolution, 6-chloroanthranilic acid (5 g, 29 mmol) was added forming a suspension. This mixture was added to a separate flask containing a suspension of paraformaldehyde (1.22 g, 43.5 mmol) in MeOH (35 mL), and the resulting solution was stirred for 5 h at room temperature. Sodium borohydride (1.1 g, 29 mmol) was added and the mixture refluxed for 3 h. The cooled mixture was hydrolyzed with 1 M potassium hydroxide then neutralized to pH 3 using 2 M HCl. The precipitate was filtered to yield 2-chloro-6-methylamino benzoic acid (2.2 g, 41%).

Workup

  1. customforming a suspension
  2. additionThis mixture was added to a separate flask
  3. additioncontaining
  4. temperaturethe mixture refluxed for 3 h
  5. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-e9687a4f51414aa9a4ed993479f50834
Source dataset
uspto-grants-2005_01
Patent number
US06844435B2

Reaction notes

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