Ammonia → 2-(3-(Pyridin-2-yl)phenyl)benzo[d]oxazole-7-carboxamide

HRID 415293Notes

Reaction equation

HRID 415293 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([C:13]2[O:14][C:15]3[C:21]([C:22]([O:24]C)=O)=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)[CH:10]=[CH:11][CH:12]=1.[NH3:26]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([C:13]2[O:14][C:15]3[C:21]([C:22]([NH2:26])=[O:24])=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66621080Methyl 2-(3-(pyridin-2-yl)phenyl)benzo[d]oxazole-7-carboxylate

Product 1

HCID 666211852-(3-(Pyridin-2-yl)phenyl)benzo[d]oxazole-7-carboxamideYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(3-(pyridin-2-yl)phenyl)benzo[d]oxazole-7-carboxylate (150 mg, 0.43 mmol) was added to ammonia in methanol (30 mL) and the mixture was stirred at room temperature for 3 days. Then the solid was filtered, washed with methanol, dried in vacuum. 100 mg of 2-(3-(pyridin-2-yl)phenyl)benzo[d]oxazole-7-carboxamide was obtained, yield: 74%. 1H-NMR (400 MHz, DMSO-d6) δ 7.44-7.47 (t, J=5.2 Hz, 1H), 7.50-7.54 (t, J=8.0 Hz, 1H), 7.76-7.88 (m, 3H), 7.96-8.01 (m, 3H), 8.12-8.14 (d, J=7.6 Hz, 1H); 8.35-8.39 (t, J=8.0 Hz, 2H); 8.76-8.77 (d, J=2.8 Hz, 1H); 9.01 (s, 1H); LC-MS (ESI) m/z: 316 (M+1)+.

Workup

  1. filtrationThen the solid was filtered
  2. washwashed with methanol
  3. customdried in vacuum

Sources & evidence

ORD record
ord-9f6c0611c3e843c5aebf004e973f9de5
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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