Water → 5-(Oxazolo[5,4-c]pyridin-2-yl)thiophen-2-amine

HRID 2265033Notes

Reaction equation

HRID 2265033 reaction equation
[N+:1]([C:4]1[S:8][C:7]([C:9]2[O:10][C:11]3[CH:12]=[N:13][CH:14]=[CH:15][C:16]=3[N:17]=2)=[CH:6][CH:5]=1)([O-])=O.[NH4+].[Cl-].O>[Fe].CO>[N:17]1[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[O:10][C:9]=1[C:7]1[S:8][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 596799322-(5-Nitrothiophen-2-yl)oxazolo[5,4-c]pyridine

Product 1

HCID 596801935-(Oxazolo[5,4-c]pyridin-2-yl)thiophen-2-amineYield 35%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(5-nitrothiophen-2-yl)oxazolo[5,4-c]pyridine (170 mg, 0.69 mmol), NH4Cl (199 mg, 3.73 mmol), iron powder (328 mg, 5.87 mmol), H2O (10 mL) and methanol (40 mL) was heated to reflux for 6 hrs under N2. The mixture was concentrated in vacuo followed by addition of 100 mL of water and left overnight at 4° C. The precipitate was collected by filtration and dried to give 5-(oxazolo[5,4-c]pyridin-2-yl)thiophen-2-amine as a brown solid (52 mg, yield 35%). 1HNMR (400 MHz, DMSO-d6) δ: 8.84 (1H, s); 8.40 (1H, d, J=5.2); 7.64 (1H, d, J=4); 7.57 (1H, d, J=5.2), 7.06 (2H, s), 1.09 (1H, d, J=4.4).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 hrs under N2
  3. concentrationThe mixture was concentrated in vacuo
  4. additionfollowed by addition of 100 mL of water
  5. filtrationThe precipitate was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-1100f837e76f465ea107d4bdd8f23282
Source dataset
uspto-grants-2010_12
Patent number
US07855289B2

Reaction notes

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