Ammonium formate → HCID 57995589, compound

HRID 385318Notes

Reaction equation

HRID 385318 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)=[CH:10][C:9]([CH:22]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:8][C:7]=2[N+:32]([O-])=O)[CH2:3][CH2:2]1.C([O-])=O.[NH4+]>C1(C)C=CC=CC=1.O.[Fe]>[NH2:32][C:7]1[CH:8]=[C:9]([CH:22]([CH2:28][CH:29]([CH3:30])[CH3:31])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:10]=[C:11]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:17]=2)[C:6]=1[O:5][CH2:4][CH:1]1[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57995553HCID 57995553, compound

Product 1

HCID 57995589HCID 57995589, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22272177Toluene waterSolvent

Procedure

Ethyl 2-(6-(cyclopropylmethoxy)-5-nitro-4′-(trifluoromethyl)biphenyl-3-yl)-4-methylpentanoate (300 mg, 0.626 mmo) was taken in 30 ml of Toluene:Water (1:1) and to it added Fe powder (203 mg, 3.62 mmol), Ammonium formate (228 mg, 3.62 mmol). The reaction mixture was refluxed for 3 h and then filtered through celite. The toluene was distilled off under reduced pressure and the crude residue was purified by column chromatography using Ethyl acetate:hexane (2:3) as eluent provided 220 mg of ethyl 2-(5-amino-6-(cyclopropylmethoxy)-4′-(trifluoromethyl)biphenyl-3-yl)-4-methylpentanoate. 1H NMR (CDCl3): δ 7.40-7.20 (m, 5H), 6.90 (s 1H), 4.50 (bs, 2H), 4.15 (q, 2H), 3.60 (t, 1H), 3.45 (d, 2H), 1.95-2.00 (m, 1H), 1.75-1.80 (m, 1H), 1.45-1.50 (m, 1H), 1.20 (t, 3H), 1.00 (m, 6H), 0.35-0.25 (m, 5H). Mass: (450, M+1, 100%).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. filtrationfiltered through celite
  3. distillationThe toluene was distilled off under reduced pressure
  4. customthe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-ad350181165649c7be211a145bf52f40
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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