4-Methyl-N-(3,4,5-trimethoxybenzyl)aniline → 4-Methoxy-N-(3,4,5-trimethoxybenzyl)aniline

HRID 1647300Notes

Reaction equation

HRID 1647300 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([N:7]=[CH:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+].CC1C=CC(NCC2C=C(OC)C(OC)=C(OC)C=2)=CC=1>>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([NH:7][CH2:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 3737984-Methyl-N-(3,4,5-trimethoxybenzyl)anilineHCID 373989151221-92-0HCID 4311764Sodium borohydride

Product 1

HCID 3647164-Methoxy-N-(3,4,5-trimethoxybenzyl)anilineYield 93.5%

Procedure

From 108c (10.8 g, 35.8 mmol) and NaBH4 (6.8 g, 179 mmol), a similar procedure as described for 109a gave 109c (10.1 g, 93.5%) as pale purple crystals. 1H NMR (200 MHz, CDCl3) δ6.79 (d, J=8 Hz, 2H), 6.62 (d, J=8 Hz, 2H), 6.61 (s, 2H), 4.21 (s, 2H), 3.84 (s, 9H), 3.74 (s, 3H). CIMS (isobutane) m/e 304 (MH+, 20).

Sources & evidence

ORD record
ord-be825ab54b76401ab0168a5c56006e1c
Source dataset
uspto-grants-1995_07
Patent number
US05430062

Reaction notes

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