Water → HCID 59680106, compound

HRID 1667025Notes

Reaction equation

HRID 1667025 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[CH:13]=[N:14][CH:15]=[CH:16][C:17]=3[N:18]=2)=[CH:6][CH:5]=1)([O-])=O.[NH4+].[Cl-].O>[Fe].CO>[N:18]1[C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[O:11][C:10]=1[C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 59680062HCID 59680062, compound

Product 1

HCID 59680106HCID 59680106, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(4-nitrophenyl)oxazolo[5,4-c]pyridine (610 mg, 2.5 mmol), NH4Cl (1.2 g, 22.4 mmol), iron powder (0.76 g, 13.6 mmol), H2O (13 mL) and methanol (51 mL) was heated to reflux for 6 h under N2. The mixture was concentrated in vacuo and purified by chromatography on silica gel (eluted with EA/PE=3:1) to give 4-(oxazolo[5,4-c]pyridin-2-yl)benzenamine as light brown powder (340 mg, yield 64%). 1H NMR (400 MHz, DMSO-d6) δ: 8.95 (1H, s); 8.46 (1H, d, J=5.2); 7.92 (2H, d, J=8.8); 7.69 (1H, d, J=5.6), 6.71 (2H, d, J=8.8), 6.19 (2H, s); MS (ESI) calcd for C12H9N3O (m/z): 211, found: 212 [M+H]+

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 h under N2
  3. concentrationThe mixture was concentrated in vacuo
  4. custompurified by chromatography on silica gel (eluted with EA/PE=3:1)

Sources & evidence

ORD record
ord-a274cbd874f6472cb575d182eb2327b7
Source dataset
uspto-grants-2011_10
Patent number
US08044198B2

Reaction notes

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