Ammonium Chloride → 2-Thiazolo[4,5-c]pyridin-2-yl-phenylamine

HRID 1697154Notes

Reaction equation

HRID 1697154 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:18]=1)([O-])=O.[NH4+].[Cl-]>CO.O.[Fe]>[S:11]1[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:18]=[C:10]1[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH2:1]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 596801882-(2-Nitrophenyl)thiazolo[4,5-c]pyridine

Product 1

HCID 596799612-Thiazolo[4,5-c]pyridin-2-yl-phenylamineYield 73%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

A suspension of 2-(2-nitrophenyl)thiazolo[4,5-c]pyridine (1.170 g, 4.6 mmol), Fe powder (1.26 g, 22.8 mmol) and NH4Cl (1.97 g, 36.8 mmol) in CH3OH:H2O (4:1, 80 mL) was refluxed for 6 hrs. The mixture was filtered and the filtrate was evaporated in vacuo. The residue was poured into water. The precipitate was collected by filtration, and washed with water (20 mL×3) to afford 2-thiazolo[4,5-c]pyridin-2-yl-phenylamine as a yellow solid (0.760 g, yield: 73%).

Workup

  1. temperaturewas refluxed for 6 hrs
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. additionThe residue was poured into water
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water (20 mL×3)

Sources & evidence

ORD record
ord-062dc576f9a642e38815bc45e8e34897
Source dataset
uspto-grants-2012_04
Patent number
US08163908B2

Reaction notes

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