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

HRID 1647299Notes

Reaction equation

HRID 1647299 reaction equation
[CH2:1]([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)[CH3:2].[BH4-].[Na+].CC1C=CC(NCC2C=C(OC)C(OC)=C(OC)C=2)=CC=1>>[CH2:1]([C:3]1[CH:22]=[CH:21][C:6]([NH:7][CH2:8][C:9]2[CH:10]=[C:11]([O:19][CH3:20])[C:12]([O:17][CH3:18])=[C:13]([O:15][CH3:16])[CH:14]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 3

HCID 3737984-Methyl-N-(3,4,5-trimethoxybenzyl)anilineHCID 373991151221-91-9HCID 4311764Sodium borohydride

Product 1

HCID 3738004-Ethyl-N-(3,4,5-trimethoxybenzyl)anilineYield 76.6%

Procedure

From 108b (7.0 g, 23.4 mmol) and NaBH4 (4.4 g, 117 mmol), a similar procedure as described for 109a gave 109b (5.4 g, 76.6%) as white crystals: mp 64°-6° C. after recrystallization from ethanol. 1H NMR (200 MHz, CDCl3) δ7.03 (d, J=8 Hz, 2H), 6.61 (s, 2H), 6.62 (d, J=8 Hz, 2H), 4.24 (s, 2H), 3.84 (s, 9H) 2.55 (q, J=8 Hz, 2H), 1.19 (t, J=Hz, 3H). EIMS m/e 301 (M+, 34).

Sources & evidence

ORD record
ord-d7e9e079dc134b6b8e4bfdad99807e15
Source dataset
uspto-grants-1995_07
Patent number
US05430062

Reaction notes

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