6-Nitroveratraldehyde → 1-(2'-Nitro-4',5'-dimethoxybenzylidene)-7-nitro-2-tetralone

HRID 1602201Notes

Reaction equation

[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][C:10](=[O:14])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:15]([C:18]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[CH:22][C:19]=1[CH:20]=O)([O-:17])=[O:16]>>[N+:15]([C:18]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[CH:22][C:19]=1[CH:20]=[C:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=2)[CH2:8][CH2:9][C:10]1=[O:14])([O-:17])=[O:16]

Participants

Reactant 2

HCID 885056-Nitroveratraldehyde

HCID 113214437-Nitro-2-tetralone

Product 1

HCID 540779171-(2'-Nitro-4',5'-dimethoxybenzylidene)-7-nitro-2-tetralone

Procedure

Prepared from 7-nitro-2-tetralone and 2-nitro-4,5-dimethoxybenzaldehyde; mp 125° C.; IR (Nujol): 1724, 1540, 1545; 1H NMR: δ2.69 (2H, t), 3.16 (2H t), 3.59 (3H, s), 4.01 (3H, s), 6.45 (1H, s), 7.41 (1H, d, J=8.1), 7.68 (1H, d, J=2.2), 7.72 (1H, s), 7.94-7.99 (1H, dd, J=8.4, 2.2), 8.08 (1H, s); 13C NMR: δ28.4, 36.9, 56.9, 57.0, 108.7, 111.6, 123.2, 124.2, 126.1, 129.7, 132.5, 133.9, 135.8, 141.4, 145.8, 146.8, 150.1, 154.1, 198.4.

Sources & evidence

ORD record: ord-9ba748c6c86f4b668e643d47fe5a56ec
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05981541

Reaction notes

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