4-Nitrophenol → HCID 14742806, compound

HRID 1651232Notes

Reaction equation

HRID 1651232 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)=[C:8](/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])[CH:7]=[CH:6]2.[N+:26]([C:29]1[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=1)([O-:28])=[O:27].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:26]([C:29]1[CH:34]=[CH:33][C:32]([O:24][C:23](=[O:25])/[CH:22]=[CH:21]/[C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:9]=2[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:31][CH:30]=1)([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14742794HCID 14742794, compound

Product 1

HCID 14742806HCID 14742806, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 113, (E)-3-[6-methoxy-1-(4-methoxyphenyl)-2-naphthalenyl]-2-propenoic acid (1.4 g) was reacted with 4-nitrophenol (0.64 g) in dichloromethane (25 mL) in the presence of 1,3-dicyclohexylcarbodiimide (0.87 g) overnight at room temperature to give, after the normal work up and crystallization of the crude product from 2-propanol, 1.6 g of (E)-3-[6-methoxy-1-(4-methoxyphenyl)-2-naphthalenyl]-2-propenoic acid 4-nitrophenyl ester, mp 160°-161° C. Anal. Calcd for C27H21NO6 : C, 71.20; H, 4.65; N, 3.08 Found: C, 70.87; H, 4.89; N, 3.06

Workup

  1. customto give
  2. customafter the normal work up and crystallization of the crude product from 2-propanol, 1.6 g of (E)-3-[6-methoxy-1-(4-methoxyphenyl)-2-naphthalenyl]-2-propenoic acid 4-nitrophenyl ester, mp 160°-161° C

Sources & evidence

ORD record
ord-47b3dfcb145d46d6b2a8cb744b52bf9d
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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