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

HRID 842094Notes

Reaction equation

HRID 842094 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′-carbonyl diimidazole (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), 1 N 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.

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), 1 N HCl (50 ml) and brine (50 ml)
  4. dry with materialdried over CaSO4
  5. customevaporated in-vacuo

Sources & evidence

ORD record
ord-5abd6d711a424e84975c7298d7e8a334
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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