1,1'-Carbonyldiimidazole → N-(2-hydroxy-3-nitrophenyl)-3-cyclopentyloxy-4-methoxyphenylacetamide

HRID 1377544Notes

Reaction equation

HRID 1377544 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][C:16]([OH:18])=O)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([N+:38]([O-:40])=[O:39])[C:33]=1[OH:41]>ClCCl.O>[OH:41][C:33]1[C:34]([N+:38]([O-:40])=[O:39])=[CH:35][CH:36]=[CH:37][C:32]=1[NH:31][C:16](=[O:18])[CH2:15][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:8]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 51272912-Amino-6-nitrophenolHCID 107293423-Cyclopentyloxy-4-methoxyphenylacetic acid

Product 1

HCID 22618278N-(2-hydroxy-3-nitrophenyl)-3-cyclopentyloxy-4-methoxyphenylacetamideYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 3-cyclopentyloxy-4-methoxyphenylacetic acid (1.00 g) and 1,1'-carbonyldiimidazole (821 mg) in dichloromethane (5 ml) was stirred at room temperature, under argon, for 2 hours. The resulting solution was added to a stirred solution of 2-amino-6-nitrophenol (723 mg) in dichloromethane (10 ml) and the mixture stirred at room temperature, under argon, overnight. The reaction mixture was diluted with water (100 ml) and extracted with dichloromethane (3×50 ml). The combined organic extracts were washed with water (100 ml), 1N HCl (50 ml) and brine (50 ml), dried over CaSO4 and evaporated in-vacuo to yield the title compound (1.05 g, 68%) as an orange solid. δH (250 MHz;d6DMSO), 1.58-1.97 (8H,m,4 ×CH2), 3.73 (2H,s,CH2), 3.87 (3H,s,OMe), 4.79 (1H,m,CH), 6.78-6.93 (3H,m,ArH), 6.98 (1H,t,ArH), 7.78 (1H,dd,ArH), 7.95 (1H,bs,CONH), 8.71 (1H,dd,ArH), 10.5 (1H,bs,ArOH).

Workup

  1. stirringthe mixture stirred at room temperature, under argon, overnight
  2. extractionextracted with dichloromethane (3×50 ml)
  3. washThe combined organic extracts were washed with water (100 ml), 1N HCl (50 ml) and brine (50 ml)
  4. dry with materialdried over CaSO4
  5. customevaporated in-vacuo

Sources & evidence

ORD record
ord-cfa667be2e4d468597a9c6620036fd91
Source dataset
uspto-grants-1997_09
Patent number
US05665737

Reaction notes

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