Ammonium Chloride → 2-amino-N-(2-chloropyridin-3-yl)-5-methylbenzamide

HRID 44237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 44237
[Cl:1][C:2]1[C:7]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=2[N+:17]([O-])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl-].[NH4+]>CO.C(OCC)(=O)C.[Zn]>[NH2:17][C:11]1[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:10]=1[C:9]([NH:8][C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=1)=[O:20]

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 3440161N-(2-chloropyridin-3-yl)-5-methyl-2-nitrobenzamide

Produkt 1

HCID 140754362-amino-N-(2-chloropyridin-3-yl)-5-methylbenzamideAusbeute 72,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of N-(2-chloropyridin-3-yl)-5-methyl-2-nitrobenzamide (5.07 g, 17.38 mmol), ammonium chloride (5.30 g, 99.1 mmol) in methanol (170 mL) was treated with zinc dust (8.1 g, 123.9 mmol) and stirred for 1 hour at room temperature. The mixture was diluted with ethyl acetate (300 mL) then filtered and concentrated under reduced pressure. The crude product was dissolved in refluxing methanol (350 mL) then cooled to room temperature and treated with water (300 mL) to give a white precipitate which was filtered, washed with water (50 mL) and dried under high vacuum at 60° C. to give 2-amino-N-(2-chloropyridin-3-yl)-5-methylbenzamide (3.3 g). M.p.=187-190° C.; 400 MHz 1H NMR (DMSO-d6) δ: 9.87 (s, 1H), 8.25 (dd, J=2.0, 4.8 Hz, 1H), 8.02 (dd, J=2.0, 8.0 Hz, 1H), 7.52 (s, 1H), 7.45 (dd, J=4.8, 8.0 Hz, 1H), 7.04 (dd, J=2.0, 8.8 Hz, 2H), 6.67 (d, J=8.4 Hz, 1H), 6.21 (s, 2H), 2.19 (s, 3H); LCMS [M+H]: 262.

Aufarbeitung

  1. filtrationthen filtered
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe crude product was dissolved
  4. temperaturein refluxing methanol (350 mL)
  5. temperaturethen cooled to room temperature
  6. additiontreated with water (300 mL)
  7. customto give a white precipitate which
  8. filtrationwas filtered
  9. washwashed with water (50 mL)
  10. customdried under high vacuum at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-baa8cf71640d4d32a2da16e6b83566db
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541407B2

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