4-Nitrophenol → 2-Acetyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester

HRID 564727Notes

Reaction equation

HRID 564727 reaction equation
[CH3:1][O:2][C:3]([C:7]1[O:20][C:10]2[C:11]([O:18][CH3:19])=[N:12][CH:13]=[C:14]([C:15]([OH:17])=[O:16])[C:9]=2[CH:8]=1)([O:5][CH3:6])[CH3:4].[CH:21]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[C:23]([OH:30])[CH:22]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[N+:27]([C:26]1[CH:21]=[CH:22][C:23]([O:16][C:15]([C:14]2[C:9]3[CH:8]=[C:7]([C:3]([O:5][CH3:6])([O:2][CH3:1])[CH3:4])[O:20][C:10]=3[C:11]([O:18][CH3:19])=[N:12][CH:13]=2)=[O:17])=[CH:24][CH:25]=1)([O-:29])=[O:28].[N+:27]([C:26]1[CH:25]=[CH:24][C:23]([O:30][C:15]([C:14]2[C:9]3[CH:8]=[C:7]([C:3](=[O:2])[CH3:4])[O:20][C:10]=3[C:11]([O:18][CH3:19])=[N:12][CH:13]=2)=[O:16])=[CH:22][CH:21]=1)([O-:29])=[O:28]

Participants

7

Reactant 3

HCID 9804-NitrophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 221128202-(1,1-Dimethoxyethyl)-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid

Product 2

HCID 541659832-Acetyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl esterHCID 545256332-(1,1-Dimethoxyethyl)-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

2-(1,1-Dimethoxyethyl)-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (0.66 g), p-nitrophenol (0.32 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.49 g) and 4-dimethylaminopyridine (catalytic) in dry dichloromethane (40 ml) were stirred overnight at room temperature. The mixture was diluted with dichloromethane (50 ml), washed with water (100 ml), dried over magnesium sulfate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 33% hexane in ethyl acetate to 100% ethyl acetate gave 2-(1,1-dimethoxyethyl)-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester (0.51 g) and 2-acetyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester (0.20 g) as white solids.

Workup

  1. washwashed with water (100 ml)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customPurification by column chromatography on silica eluting with 33% hexane in ethyl acetate to 100% ethyl acetate

Sources & evidence

ORD record
ord-be1e3489d31d4b07b1601dd1da532f03
Source dataset
uspto-grants-2001_01
Patent number
US06169090A

Reaction notes

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