3,4,5-Trimethoxybenzaldehyde → 158319-78-9

HRID 1647296Notes

Reaction equation

HRID 1647296 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=O.[CH2:15]([O:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)[CH3:16].CC1C=CC(N=CC2C=C(OC)C(OC)=C(OC)C=2)=CC=1>>[CH2:15]([O:17][C:18]1[CH:24]=[CH:23][C:21]([N:22]=[CH:6][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=2)=[CH:20][CH:19]=1)[CH3:16]

Participants

4

Reactant 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 90764-EthoxyanilineHCID 15657369HCID 15657369, compound

Product 1

HCID 373990158319-78-9

Procedure

From 3,4,5, trimethoxybenzaldehyde 106 (6.0 g, 30 mmol) and 4-ethoxyaniline 107d (4.1 g, 30 mmol), a similar procedure as described for 108a (5.9 g, 97.4%) as yellow crystals: mp 75°-7° C. after recrystallization from ethanol. 1H NMR (200 MHz, CDCl3) δ8.37 (s, 1H), 7.21 (d, J=8 Hz, 2H), 7.14 (s, 2H), 6.91 (d, J=8 Hz, 2H), 4.05 (q, J=6 Hz, 2H), 3.94 (s, 6H), 3.91 (s, 3H), 1.43 (t, J=6 Hz, 3H). EIMS m/e 315 (M+, 93).

Workup

  1. custommp 75°-7° C. after recrystallization from ethanol

Sources & evidence

ORD record
ord-5895511bd0e24216981b39a9897f857e
Source dataset
uspto-grants-1995_07
Patent number
US05430062

Reaction notes

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