P-Anisidine → 2-Hydroxy-5-[(4-methoxyphenylamino)methyl]benzoic Acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH:10]([C:12]1[CH:20]=[C:16]([C:17]([OH:19])=[O:18])[C:15]([OH:21])=[CH:14][CH:13]=1)=O.C([BH3-])#N.[Na+].C(OCC)(=O)C>CO.CN1CCCC1=O>[OH:21][C:15]1[CH:14]=[CH:13][C:12]([CH2:10][NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:20][C:16]=1[C:17]([OH:19])=[O:18]Participants
Procedure
p-Anisidine (1.3 g, 10.6 mmol) was dissolved in methanol (20 mL) and 5-formylsalicylic acid (1.75 g, 10.6 mmol) was added and the resulting mixture was stirred at room temperature for 16 hours. The solid formed was isolated by filtration, re-dissolved in N-methyl pyrrolidone (20 mL) and methanol (2 mL). To the mixture was added sodium cyanoborohydride (1.2 g) and the mixture was heated to 70° C. for 3 hours. To the cooled mixture was added ethyl acetate (100 mL) and the mixture was extracted with water (100 mL) and saturated aqueous ammonium chloride (100 mL). The combined aqueous phases were concentrated in vacuo and a 2 g aliquot was purified by SepPac chromatography eluting with mixtures of aetonitrile and water containing 0.1% trifluoroacetic acid to afford the title compound.
Workup
- customThe solid formed
- customwas isolated by filtration
- temperaturethe mixture was heated to 70° C. for 3 hours
- extractionthe mixture was extracted with water (100 mL) and saturated aqueous ammonium chloride (100 mL)
- concentrationThe combined aqueous phases were concentrated in vacuo
- customa 2 g aliquot was purified by SepPac chromatography
- washeluting with mixtures of aetonitrile and water containing 0.1% trifluoroacetic acid
Sources & evidence
- ORD record
- ord-c72f71c63c074a2a9a6e5f80193b0f05
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07879893B2
Reaction notes
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