Water → 3-(Thiazolo[4,5-c]pyridin-2-yl)benzenamine

HRID 1667015Notes

Reaction equation

HRID 1667015 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[S:11][C:12]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=3[N:18]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[NH4+].[Cl-].O>[Fe].CO>[S:11]1[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:18]=[C:10]1[C:6]1[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 217706492-(3-Nitrophenyl)thiazolo[4,5-c]pyridine

Product 1

HCID 217706533-(Thiazolo[4,5-c]pyridin-2-yl)benzenamineYield 63%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(3-nitrophenyl)thiazolo[4,5-c]pyridine (1.53 g, 5.9 mmol), NH4Cl (2.76 g, 51.6 mmol), iron powder (1.80 g, 32.2 mmol), H2O (30 mL) and methanol (120 mL) was heated to reflux for 5.5 h under N2. The mixture was filtered and the filtrate was diluted with H2O (400 mL). The precipitate was collected by filtration and dried in vacuo to afford 3-(thiazolo[4,5-c]pyridin-2-yl)benzenamine as a brown solid (841 mg, 63%). 1HNMR (400 MHz, DMSO-d6) δ: 9.28 (1H, s); 8.52 (1H, s); 8.21 (1H, s); 7.23-7.38 (3H, d), 6.79 (1H, s), 5.51 (2H, s); MS (ESI) calcd. for C12H9N3S (m/z): 227, found: 228 [M+H]P

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5.5 h under N2
  3. filtrationThe mixture was filtered
  4. additionthe filtrate was diluted with H2O (400 mL)
  5. filtrationThe precipitate was collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-ddff8da0e8404c9c93de8ab8312e9ff4
Source dataset
uspto-grants-2011_10
Patent number
US08044198B2

Reaction notes

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