4-Nitro-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester → 4-Amino-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester

HRID 1830741Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1830741
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[C:6]([O:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:5]=1>CO.[Cl-].[NH4+].C(OCC)(=O)C.[Zn]>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([O:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:5]=1

Komponenten

6

Edukt 1

HCID 672560514-Nitro-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester

Produkt 1

HCID 433801884-Amino-3-(pyridin-3-ylmethoxy)-benzoic acid methyl esterAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a stirred, cooled (about 0° C.) solution of 4-nitro-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester (288 mg, 1.0 mmol) in methanol (2 mL) and saturated aqueous ammonium chloride (1 mL) was added zinc dust (131 mg, 2.0 mmol). After stirring for 12 hours, the reaction was diluted with 30 mL of ethyl acetate and washed with 30 mL of 10% aqueous sodium carbonate (2×30 mL), brine (1×30 mL), then dried (MgSO4), and filtered. The filtered solution was concentrated under reduced pressure to yield the desired product as a yellow solid (97% yield). 1H-NMR (400 MHz, CDCl3) δ8.78 (s, 1H), 8.61 (d, 1H, 7.79 (d, 1H), 7.59 (m, 2H), 7.39 (m, 1H), 6.71 (d, 1H), 5.18 (s, 2H), 4.28 (br s, 2H), 3.85 (s, 3H).

Aufarbeitung

  1. washwashed with 30 mL of 10% aqueous sodium carbonate (2×30 mL), brine (1×30 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtered solution was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-eee3ec3d0c7044db88546e4262adb969
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07067506B2

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