Hydrochloric Acid → 7-Amino-6-chloro-1,3-benzodioxole-4-carboxylic acid

HRID 559135Notes

Reaction equation

HRID 559135 reaction equation
C([NH:4][C:5]1[C:10]2[O:11][CH2:12][O:13][C:9]=2[C:8]([C:14]([O:16]C)=[O:15])=[CH:7][C:6]=1[Cl:18])(=O)C.[OH-].[K+].Cl>O>[NH2:4][C:5]1[C:10]2[O:11][CH2:12][O:13][C:9]=2[C:8]([C:14]([OH:16])=[O:15])=[CH:7][C:6]=1[Cl:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22662759Methyl 7-(acetylamino)-6-chloro-1,3-benzodioxole-4-carboxylate

Product 1

HCID 226627477-Amino-6-chloro-1,3-benzodioxole-4-carboxylic acidYield 96.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Intermediate (2-d) (18.2 g) was added to a solution of KOH (37.6 g) in water (380 ml). The resulting reaction mixture was stirred and refluxed for 3 hours. The mixture was cooled, acidified with hydrochloric acid, and the resulting precipitate was filtered off, washed with water, suspended in ACN, filtered off, then dried, yielding 14 g (>95%) of 7-amino-6-chloro-1,3-benzodioxole-4-carboxylic acid (intermediate 2-e). In an analogous way, 3,4-dihydro-9-iodo-2H-1,5-benzodioxepin-6-amine (intermediate 2-f) was prepared.

Workup

  1. customThe resulting reaction mixture
  2. temperaturerefluxed for 3 hours
  3. temperatureThe mixture was cooled
  4. filtrationthe resulting precipitate was filtered off
  5. washwashed with water
  6. filtrationfiltered off
  7. customdried

Sources & evidence

ORD record
ord-607489f5fd4f4aa8a3d141339f74c8eb
Source dataset
uspto-grants-2011_11
Patent number
US08063070B2

Reaction notes

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