P-Anisidine → 2-Hydroxy-5-[(4-methoxyphenylamino)methyl]benzoic Acid

HRID 1361007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361007
[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]

Komponenten

7

Edukt 4

HCID 7732P-AnisidineHCID 8857Ethyl AcetateHCID 692265-Formylsalicylic acidHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 574570412-Hydroxy-5-[(4-methoxyphenylamino)methyl]benzoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customThe solid formed
  2. customwas isolated by filtration
  3. temperaturethe mixture was heated to 70° C. for 3 hours
  4. extractionthe mixture was extracted with water (100 mL) and saturated aqueous ammonium chloride (100 mL)
  5. concentrationThe combined aqueous phases were concentrated in vacuo
  6. customa 2 g aliquot was purified by SepPac chromatography
  7. washeluting with mixtures of aetonitrile and water containing 0.1% trifluoroacetic acid

Quellen und Nachweise

ORD-Eintrag
ord-c72f71c63c074a2a9a6e5f80193b0f05
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879893B2

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