Ethanol → HCID 18416154, compound

HRID 990940Notes

Reaction equation

HRID 990940 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.O.O.[Cl-].[Ca+2].[Cl-].CCO>[Zn].O>[NH2:9][C:7]1[CH:6]=[CH:5][C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 6093260Calcium chloride, dihydrateHCID 18416158HCID 18416158, compound

Product 1

HCID 18416154HCID 18416154, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

This compound was prepared by General Method 10 (EXAMPLE 19) from (2-methoxy-4-nitrophenyl)-(4-methoxybenzyl)amine (1.92 g, 6.65 mmol), zinc dust (1.87 g, 28.6 mmol), and calcium chloride dihydrate (2.10 g, 14.3 mmol) in 350 mL 95:5 EtOH:water to afford 1.23 g (70%) of (4-amino-2-methoxyphenyl)-(4-methoxybenzyl)amine, a light purple solid, after flash chromatography (CH2Cl2:MeOH 19:1). Data for (4-amino-2-methoxyphenyl)-(4-methoxybenzyl)amine: Rf 0.80 (19:1 CH2Cl2:MeOH); 1H NMR (400 MHz, CDCl3) δ 7.30 (d, 2H, J=8.6), 6.87 (d, 2H, J=8.6), 6.47 (d, 1H, J=8.1), 6.28 (d, 1H, J=2.4), 6.23 (dd, 1H, J=8.1, 2.4), 4.20 (s, 2H), 4.10 (v broad s, 1H), 3.80 (s, 3H), 3.79 (s, 3H), 3.31 (broad s, 2H).

Sources & evidence

ORD record
ord-ca85ec7f5e30499ab3f809de19f2b500
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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