4-Hydroxy-3-nitrobenzaldehyde → HCID 69268372, compound

HRID 2222364Notes

Reaction equation

HRID 2222364 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][O:14][CH2:15][CH2:16][O:17][CH2:18]Cl.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[CH2:25][C:26]#[N:27]>>[CH3:20][O:21][C:22]1[CH:23]=[C:24](/[C:25](=[CH:6]/[C:5]2[CH:8]=[CH:9][C:2]([O:1][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=2)/[C:26]#[N:27])[CH:28]=[CH:29][C:30]=1[O:31][CH3:32]

Participants

4

Reactant 3

HCID 181694-Hydroxy-3-nitrobenzaldehydeHCID 667273,4-DimethoxybenzeneacetonitrileHCID 775901-(Chloromethoxy)-2-methoxyethane

Product 1

HCID 69268372HCID 69268372, compoundYield 40%

Procedure

The hydroxyl group of 4-hydroxy-3-nitrobenzaldehyde (500 mg) was protected by use of 2-methoxyethoxymethyl chloride (374 mg) in accordance with (production process 1), to thereby produce an MEM form (605 mg, yield: 70%). The resultant MEM form (255 mg) and 3,4-dimethoxybenzyl cyanide (177 mg) were subjected to condensation in accordance with process B of (production process 2), to thereby produce (Z)-2-(3,4-dimethoxy-phenyl)-3-[4-(2-methoxy-ethoxymethoxy)-3-nitro-phenyl]-acrylonitrile (153 mg, yield: 40%). The thus-produced (Z)-2-(3,4-dimethoxy-phenyl)-3-[4-(2-methoxy-ethoxymethoxy)-3-nitro-phenyl]-acrylonitrile (140 mg) was subjected to deprotection in accordance with (production process 3), to thereby produce the target product (72 mg, yield: 60%).

Workup

  1. customto thereby produce an MEM form (605 mg, yield: 70%)

Sources & evidence

ORD record
ord-90b95d3d93ad482d88fdd99751ba1945
Source dataset
uspto-grants-2008_05
Patent number
US07371773B2

Reaction notes

Loading…