3,4-Dimethoxybenzeneacetonitrile → (Z)-2-(3,4-dimethoxy-phenyl)-3-[2-(2-methoxy-ethoxymethoxy)-5-nitro-phenyl]-acrylonitrile

HRID 2222383Notes

Reaction equation

HRID 2222383 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=O.[CH3:13][O:14][CH2:15][CH2:16][O:17][CH2:18]OCl.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH2:26][C:27]#[N:28]>>[CH3:21][O:22][C:23]1[CH:24]=[C:25](/[C:26](=[CH:4]/[C:3]2[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:2]=2[O:1][CH2:18][O:17][CH2:16][CH2:15][O:14][CH3:13])/[C:27]#[N:28])[CH:29]=[CH:30][C:31]=1[O:32][CH3:33]

Participants

4

Reactant 3

HCID 667273,4-DimethoxybenzeneacetonitrileHCID 668085-NitrosalicylaldehydeHCID 19350948Methoxyethoxylmethoxyl chloride

Product 1

HCID 69274240(Z)-2-(3,4-dimethoxy-phenyl)-3-[2-(2-methoxy-ethoxymethoxy)-5-nitro-phenyl]-acrylonitrileYield 40%

Procedure

The hydroxyl group of 2-hydroxy-5-nitrobenzaldehyde (1.00 g) was protected by use of 2-methoxyethoxymethoxyl chloride (0.75 g) in accordance with (production process 1), to thereby produce an MEM form (1.10 g, yield: 65%). The resultant MEM form (510 mg) and 3,4-dimethoxybenzyl cyanide (354 mg) were subjected to condensation in accordance with process B of (production process 2), to thereby produce (Z)-2-(3,4-dimethoxy-phenyl)-3-[2-(2-methoxy-ethoxymethoxy)-5-nitro-phenyl]-acrylonitrile (330 mg, yield: 40%). The thus-produced (Z)-2-(3,4-dimethoxy-phenyl)-3-[2-(2-methoxy-ethoxymethoxy)-5-nitro-phenyl]-acrylonitrile (200 mg) was subjected to deprotection in accordance with (production process 3), to thereby produce the target product (87 mg, yield: 55%).

Workup

  1. customto thereby produce an MEM form (1.10 g, yield: 65%)

Sources & evidence

ORD record
ord-09792416f780455d9edcf8d5224213f2
Source dataset
uspto-grants-2008_05
Patent number
US07371773B2

Reaction notes

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