3,4-Dimethoxybenzeneacetonitrile → HCID 69269658, compound

HRID 2222369Notes

Reaction equation

HRID 2222369 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=O.[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:5]/[C:4]2[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([O:1][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])[CH:3]=2)/[C:26]#[N:27])[CH:28]=[CH:29][C:30]=1[O:31][CH3:32]

Participants

4

Reactant 3

HCID 667273,4-DimethoxybenzeneacetonitrileHCID 697123-Hydroxy-4-nitrobenzaldehydeHCID 775901-(Chloromethoxy)-2-methoxyethane

Product 1

HCID 69269658HCID 69269658, compoundYield 34%

Procedure

The hydroxyl group of 3-hydroxy-4-nitrobenzaldehyde (0.67 g) was protected by use of 2-methoxyethoxymethyl chloride (0.50 g) in accordance with (production process 1), to thereby produce an MEM form (0.97 g, yield: 95%). The resultant MEM form (944 mg) and 3,4-dimethoxybenzyl cyanide (673 mg) were subjected to condensation in accordance with process B of (production process 2), to thereby produce (Z)-2-(3,4-dimethoxy-phenyl)-3-[3-(2-methoxy-ethoxymethoxy)-4-nitro-phenyl]-acrylonitrile (515 mg, yield: 34%). The thus-produced (Z)-2-(3,4-dimethoxy-phenyl)-3-[3-(2-methoxy-ethoxymethoxy)-4-nitro-phenyl]-acrylonitrile (350 mg) was subjected to deprotection in accordance with (production process 3), to thereby produce the target product (267 mg, yield: 97%).

Workup

  1. customto thereby produce an MEM form (0.97 g, yield: 95%)

Sources & evidence

ORD record
ord-e60f39263b37420e9c8e2404270d8c04
Source dataset
uspto-grants-2008_05
Patent number
US07371773B2

Reaction notes

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