Hydrochloric Acid → 3-(4-amino-3-methoxyphenyl)-1-(2,6-dichlorophenyl)-1H-1,2,4-triazol-5(4H)-one

HRID 508805Notes

Reaction equation

HRID 508805 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13](=[O:14])[NH:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[C:17]([O:24][CH3:25])[CH:16]=2)=[N:10]1.Cl>CO.[Fe]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:11]2[NH:12][C:13](=[O:14])[N:9]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])[N:10]=2)=[CH:16][C:17]=1[O:24][CH3:25]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136492456HCID 136492456, compound

Product 1

HCID 1364924373-(4-amino-3-methoxyphenyl)-1-(2,6-dichlorophenyl)-1H-1,2,4-triazol-5(4H)-oneYield 82.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(2,6-dichlorophenyl)-3-(3-methoxy-4-nitrophenyl)-1H-1,2,4-triazol-5(4H)-one (0.200 g, 0.52 mmol) in methanol (10 mL) was added iron powder (0.060 g, 1.84 mmol) and conc. HCl (2 mL). The reaction mixture was stirred at RT for 2 h. The reaction mass was quenched in water, basified with saturated sodium bicarbonate solution and extracted with DCM. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 0.150 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 3.80 (s, 3H), 5.34 (s, 2H), 6.66 (d, J=7.8 Hz, 1H), 7.18-7.21 (m, 2H), 7.58 (m, 1H), 7.69 (d, J=7.8 Hz, 2H), 12.27 (s, 1H); MS (m/z): 351.05 (M)+.

Workup

  1. customThe reaction mass was quenched in water
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f2aa789c432a4018a460e6b72367182a
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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