4-Methyl-N-(3,4,5-trimethoxybenzyl)aniline → 4-Ethoxy-N-[(3,4,5-trimethoxyphenyl)methyl]aniline

HRID 1647301Notes

Reaction equation

HRID 1647301 reaction equation
[CH2:1]([O:3][C:4]1[CH:23]=[CH:22][C:7]([N:8]=[CH:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[CH:6][CH:5]=1)[CH3:2].[BH4-].[Na+].CC1C=CC(NCC2C=C(OC)C(OC)=C(OC)C=2)=CC=1>>[CH2:1]([O:3][C:4]1[CH:23]=[CH:22][C:7]([NH:8][CH2:9][C:10]2[CH:11]=[C:12]([O:20][CH3:21])[C:13]([O:18][CH3:19])=[C:14]([O:16][CH3:17])[CH:15]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 3

HCID 3737984-Methyl-N-(3,4,5-trimethoxybenzyl)anilineHCID 373990158319-78-9HCID 4311764Sodium borohydride

Product 1

HCID 3738064-Ethoxy-N-[(3,4,5-trimethoxyphenyl)methyl]anilineYield 81.9%

Procedure

From the imine 108d (5.6 g, 17.8 mmol) and NaBH4 (3.4 g, 88 mmol), a similar procedure as described for 109a gave 109d (4.6 g, 81.9%) as white crystals: mp 76°-8° C. after recrystallization from ethanol. 1H NMR (200 MHz, CDCl3) δ6.78 (d, J=8 Hz, 2H), 6.62 (d, J=8 Hz, 2H), 6.61 (s, 2H), 4.21 (s, 2H), 3.96 (q, J=6 Hz, 2 Hz), 3.84 (s, 9H), 1.37 (t, J=6 Hz, 3H). CIMS (isobutane) m/e 318 (MH+, 27).

Sources & evidence

ORD record
ord-a4ee8a6b171341c1ba4cbbefbec333c1
Source dataset
uspto-grants-1995_07
Patent number
US05430062

Reaction notes

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