Sodium Carbonate → 4-Amino-3'-methoxy[1,1'-biphenyl]-3-carboxylic acid

HRID 413247Notes

Reaction equation

HRID 413247 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]([NH2:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:12][O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([C:2]2[CH:3]=[CH:4][C:5]([NH2:11])=[C:6]([CH:10]=2)[C:7]([OH:9])=[O:8])[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 72911Benzoic acid, 2-amino-5-iodo-HCID 2734370(3-Methoxyphenyl)boronic acid

Product 1

HCID 223253354-Amino-3'-methoxy[1,1'-biphenyl]-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-iodo-2-aminobenzoic acid (2.6g; 10 mmol) in ethylene glycol dimethyl ether (DME, 20 mL) add tetrakis(triphenylphosphine)palladium(0) (150 mg) under argon. After the catalyst dissolved completely, add successively 3-methoxybenzeneboronic acid (1.65 g; 11 mmol) and sodium carbonate (1M in water, 30 mL). Heat the mixture at 80° C. for 1 hour. Cool the reaction mixture then wash with 50% EtOAc in hexane. Filter the aqueous layer through a short pad of celite to remove palladium black and carefully pour the filtrate into cold 3N hydrochloric acid (25 mL) under stirring. Collect the precipitate by filtration and air-dry to obtain 5-(3-methoxyphenyl)-2-aminobenzoic acid as a white solid.

Workup

  1. dissolutionAfter the catalyst dissolved completely
  2. temperatureCool the reaction mixture
  3. washthen wash with 50% EtOAc in hexane
  4. filtrationFilter the aqueous layer through a short pad of celite
  5. customto remove palladium black
  6. additioncarefully pour the filtrate into cold 3N hydrochloric acid (25 mL)
  7. customCollect the precipitate
  8. filtrationby filtration
  9. customair-dry

Sources & evidence

ORD record
ord-99f4457c82bc4c43b840d64d7e0c87fc
Source dataset
uspto-grants-2003_05
Patent number
US06566367B2

Reaction notes

Loading…