Acetic Acid → N-[2-Amino-4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-3,5-dimethoxy-4-methyl-benzamide

HRID 1296739Notes

Reaction equation

HRID 1296739 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([O:29][CH3:30])[C:27]=1[CH3:28])[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]=[C:19]([CH3:21])[O:18][N:17]=2)=[CH:12][C:11]=1[N+:22]([O-])=O)=[O:7].C(O)(=O)C.O>C(O)C.C(OCC)(=O)C.[Fe]>[NH2:22][C:11]1[CH:12]=[C:13]([C:16]2[N:20]=[C:19]([CH3:21])[O:18][N:17]=2)[CH:14]=[CH:15][C:10]=1[CH2:9][NH:8][C:6](=[O:7])[C:5]1[CH:25]=[C:26]([O:29][CH3:30])[C:27]([CH3:28])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 694895423,5-Dimethoxy-4-methyl-N-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-2-nitro-benzyl]-benzamide

Product 1

HCID 69491883N-[2-Amino-4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-3,5-dimethoxy-4-methyl-benzamideYield 70.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of compound 1f (2.80 g, 6.81 mmol) in a mixture of ethanol (120 mL), acetic acid (6 mL) and water (24 mL) was heated to reflux. Iron powder (1.90 g, 34 mmol) was added portionwise over 45 min. The reaction mixture was cooled to rt and diluted with ethyl acetate. The ethyl acetate solution was washed with saturated NaHCO3 solution, dried Na2SO4, and concentrated on a rotary evaporator to a volume of ˜30 mL. The solid precipitate was recovered by filtration and washed with ethyl acetate (2×). The filtrate was passed through a short silica gel column in ethyl acetate, and concentrated on a rotary evaporator. The residue was triturated with ethyl acetate and combined with the previously filtered solid to afford compound 1g (1.83 g, 70%) as a tan solid. ESI-MS m/e 383.3 (M+1).

Workup

  1. temperaturewas heated to reflux
  2. washThe ethyl acetate solution was washed with saturated NaHCO3 solution, dried Na2SO4
  3. concentrationconcentrated on a rotary evaporator to a volume of ˜30 mL
  4. filtrationThe solid precipitate was recovered by filtration
  5. washwashed with ethyl acetate (2×)
  6. concentrationconcentrated on a rotary evaporator
  7. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-302efe306caa43b299eb5ec760ca0dd1
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

Loading…