Sodium Hydroxide → HCID 59680062, compound

HRID 419890Notes

Reaction equation

HRID 419890 reaction equation
O[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1.[OH-].[Na+]>O>[N+:16]([C:13]1[CH:12]=[CH:11][C:10]([C:9]2[O:19][C:2]3[CH:3]=[N:4][CH:5]=[CH:6][C:7]=3[N:8]=2)=[CH:15][CH:14]=1)([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59680217HCID 59680217, compound

Product 1

HCID 59680062HCID 59680062, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of N-(3-hydroxypyridin-4-yl)-4-nitrobenzamide (260 mg, 1 mmol) and polyphosphoric acid (1.5 mL) was stirred at 150° C. for 6 hrs. The reaction mixture was poured into water and sodium hydroxide was added until pH=5. The precipitate was collected by filtration, washed with water until neutral and dried to give 2-(4-nitrophenyl)oxazolo[5,4-c]pyridine as brown solid (177 mg, yield: 73%). 1HNMR (400 MHz, DMSO-d6) δ: 9.21 (1H, s), 8.62 (1H, d, J=4.8 Hz), 8.51 (4H, d, J=18, 8.8 Hz), 7.95 (1H, d, J=5.2 Hz).

Workup

  1. additionwas added until pH=5
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water until neutral and
  4. customdried

Sources & evidence

ORD record
ord-bfb1bcc920984c009dc56246eabccfb2
Source dataset
uspto-grants-2012_01
Patent number
US08093401B2

Reaction notes

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