Water → Methyl 4-amino-3-(4-methoxybenzamido)benzoate

HRID 427647Notes

Reaction equation

HRID 427647 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[NH2:13])[C:6]([O:8][CH3:9])=[O:7].O.N1C=CC=CC=1.[C:21](Cl)(=[O:30])[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1>C(#N)C>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([C:21]([NH:2][C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=2[NH2:13])[C:6]([O:8][CH3:9])=[O:7])=[O:30])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7477p-Anisoyl chlorideHCID 181746453,4-Diaminobenzoic Acid Methyl Ester Hydrochloride

Product 1

HCID 10732961Methyl 4-amino-3-(4-methoxybenzamido)benzoateYield 59.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of methyl 3,4-diaminobenzoate hydrochloride (1.43 g, 6.00 mmol) in acetonitrile (100 mL) was cooled to 0° C. and treated with water (15 mL), pyridine (0.97 mL, 12 mmol), and a solution of p-anisoyl chloride (1.03 g, 6.00 mmol) in acetonitrile (25 mL). The reaction mixture was allowed to slowly warm to room temperature over 16 h. The resulting precipitate was collected and washed with acetonitrile to provide 1.07 g (59%) of the title compound.

Workup

  1. customThe resulting precipitate was collected
  2. washwashed with acetonitrile

Sources & evidence

ORD record
ord-3fc2794eee52442fb8f52fe911b58177
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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