Hydrogen Bromide → 3-(3,5-Dichlorophenylamino)-4-hydroxybenzoic acid

HRID 1859682Notes

Reaction equation

HRID 1859682 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([O:10]C)=[C:6]([NH:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)[CH:5]=1.Br.[OH-].[NH4+]>C(O)(=O)C>[Cl:19][C:17]1[CH:18]=[C:13]([NH:12][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=2[OH:10])[C:3]([OH:21])=[O:2])[CH:14]=[C:15]([Cl:20])[CH:16]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14923Ammonium HydroxideHCID 54511686HCID 54511686, compound

Product 1

HCID 186261373-(3,5-Dichlorophenylamino)-4-hydroxybenzoic acidYield 90.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-(3,5-dichlorophenylamino)-4-methoxybenzoic acid methyl ester (4.48 g, 13.74 mmol), 100 mL of concentrated HBr, and 60 mL of acetic acid was heated to reflux. After 6 days, the reaction was cooled to room temperature and concentrated aqueous ammonium hydroxide was added in portions until the pH=4. The mixture was extracted with ethyl acetate three times, and the combined extracts were washed with brine (2×) and H2O (2×) then dried over MgSO4 and stripped of solvent in vacuo. The residue was triturated with 5% ether/hexane, filtered off and dried to afford the product (3.7 g); m.p. 166-167° C.

Workup

  1. extractionThe mixture was extracted with ethyl acetate three times
  2. washthe combined extracts were washed with brine (2×) and H2O (2×)
  3. dry with materialthen dried over MgSO4
  4. customThe residue was triturated with 5% ether/hexane
  5. filtrationfiltered off
  6. customdried

Sources & evidence

ORD record
ord-5aa3ebc390824bc4873645afaf7885b2
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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