4-Nitrophenol → HCID 70089651, compound

HRID 1108313Notes

Reaction equation

HRID 1108313 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:21]([OH:23])=[O:22])=[C:7]2[C:11]=1[O:10][C:9]([CH:12]([O:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[CH3:13])=[CH:8]2.[N+:24]([C:27]1[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=1)([O-:26])=[O:25].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[N+:24]([C:27]1[CH:32]=[CH:31][C:30]([O:22][C:21]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:11]3[O:10][C:9]([CH:12]([O:14][CH:15]4[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]4)[CH3:13])=[CH:8][C:7]=23)=[O:23])=[CH:29][CH:28]=1)([O-:26])=[O:25]

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18784857HCID 18784857, compound

Product 1

HCID 70089651HCID 70089651, compoundYield 27.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Prepared from 7-methoxy-2-(1-methyl-piperidin-4-yloxymethyl)-benzofuran-4-carboxylic acid (1.9 g), 4-nitrophenol (835 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.15 g) and 4-dimethylaminopyridine (catalytic amount) in dichloromethane (40 ml). Purification by column chromatography eluting with 10% methanol in dichloromethane afforded the desired product as a pale yellow solid (720 mg).

Workup

  1. customPurification by column chromatography
  2. washeluting with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-4e27fb31524e480588356b9e11e05e49
Source dataset
uspto-grants-2000_05
Patent number
US06066657

Reaction notes

Loading…