Formic Acid → N-(5-amino-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide

HRID 2402515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2402515
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[NH:11][C:12](=[O:36])[C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[N:29]=[C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)=[CH:15][CH:14]=1.C(O)=O.C([O-])=O.[K+]>[Pt].O1CCCC1.C(O)C>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([NH:11][C:12](=[O:36])[C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[N:29]=[C:28]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)=[CH:15][CH:14]=2)[CH:4]=1

Komponenten

7

Edukt 3

HCID 284Formic AcidHCID 2735122Potassium FormateHCID 57662940N-(2-methyl-5-nitrophenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide

Produkt 1

HCID 57662960N-(5-amino-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23939PlatinumKatalysatorHCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred mixture of N-(2-methyl-5-nitrophenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide (500 mg, 1.05 mmol), formic acid (140 μL, 3.71 mmol), potassium formate (312 mg, 3.71 mmol) and 5% platinum on carbon (150 mg, catalytic) in tetrahydrofuran (10 mL) and ethanol (10 mL) was heated to reflux for 1 h. The mixture was filtered while hot through Celite and washed with hot ethanol. Water was added until the mixture became cloudy, then the volatile solvents were removed on a rotary evaporator. The solid was collected by filtration to give N-(5-amino-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide (397 mg, 85%). 1H NMR (400 MHz, DMSO-d6): δ 10.20 (s, 1H), 9.46 (s, 1H), 8.15 (d, 2H), 7.97 (d, 2H), 7.84 (m, 5H), 7.65 (m, 3H), 7.42 (m, 1H), 6.89 (d, 1H), 6.65 (d, 1H), 6.39 (dd, 1H), 2.08 (s, 3H). MS (EI) for C28H23N5O: 446.1 (MH+).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 1 h
  3. filtrationThe mixture was filtered while hot through Celite
  4. washwashed with hot ethanol
  5. additionWater was added until the mixture
  6. customthe volatile solvents were removed on a rotary evaporator
  7. filtrationThe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-84e9211995fc4fb3acf05880a53cc2f2
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796294B2

Notizen zur Reaktion

Wird geladen…