Sodium Hydroxide → 2-Amino-5-chloro-3-methoxybenzoic acid

HRID 1186093Notes

Reaction equation

HRID 1186093 reaction equation
[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([Cl:14])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+]>O1CCCC1>[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([Cl:14])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58566618Methyl 2-amino-5-chloro-3-methoxybenzoate

Product 1

HCID 545958742-Amino-5-chloro-3-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-amino-5-chloro-3-methoxybenzoate (770 mg, 3.57 mmol) was suspended in tetrahydrofuran (20 mL), 2M sodium hydroxide (5 mL) was added and the mixture was stirred at ambient temperature for 20 hours. The solution was concentrated in vacuo, then partitioned between ethyl acetate and 1M hydrochloric acid. The organic layer was washed with water, then brine, dried with sodium sulfate, decanted and concentrated in vacuo to yield 2-amino-5-chloro-3-methoxybenzoic acid.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. custompartitioned between ethyl acetate and 1M hydrochloric acid
  3. washThe organic layer was washed with water
  4. dry with materialbrine, dried with sodium sulfate
  5. customdecanted
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1edf70473893420eb539e1c3e358e451
Source dataset
uspto-grants-2014_03
Patent number
US08673897B2

Reaction notes

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