Ammonium Chloride → 4-(Thiazolo[4,5-c]pyridin-2-yl)benzenamine

HRID 1393752Notes

Reaction equation

HRID 1393752 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=3[N:18]=2)=[CH:6][CH:5]=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:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 217706482-(4-Nitrophenyl)thiazolo[4,5-c]pyridine

Product 1

HCID 217706524-(Thiazolo[4,5-c]pyridin-2-yl)benzenamineYield 60.3%

Reagents, catalysts & solvents 2

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

Procedure

2-(4-nitrophenyl)thiazolo[4,5-c]pyridine (2.57 g, 0.01 mol), iron powder (2.8 g, 0.05 mmol) and NH4Cl (4.32 g, 0.08 mol) were refluxed in CH3OH/H2O (4:1, 200 mL) for 6 h. The mixture was filtered and the filtrate was evaporated in vacuo. The residue was washed with water (30 ml) to give 4-(thiazolo[4,5-c]pyridin-2-yl)benzenamine as a white solid (1.37 g, Yield: 60%).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. washThe residue was washed with water (30 ml)

Sources & evidence

ORD record
ord-3e9de951f3d248ac9198713f5acce5c9
Source dataset
uspto-grants-2008_03
Patent number
US07345178B2

Reaction notes

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