2-Methoxy-4-nitroaniline → HCID 18416158, compound

HRID 990939Notes

Reaction equation

HRID 990939 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].[CH:13](=O)[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.[BH3-]C#N.[Na+]>C(O)(=O)C>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[NH:1][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 73372-Methoxy-4-nitroanilineHCID 312444-MethoxybenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18416158HCID 18416158, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

This compound was prepared according to General Method 3 (EXAMPLE 1) from 2-amino-5-nitroanisole (1.00 g, 5.95 mmol), p-anisaldehyde (1.62 g, 11.9 mmol), NaBH3CN (0.373 g, 5.95 mmol) in 100 mL acetic acid to afford 1.25 g (75%) of (2-methoxy-4-nitrophenyl)-(4-methoxybenzyl)amine, an orange solid, after washing the crude product with 4:1 hexanes:EtOAc. Data for (2-methoxy-4-nitrophenyl)-(4-methoxybenzyl)amine: Rf 0.80 (3:2 EtOAc:hexanes); 1NMR (500 MHz, CDCl3) δ 7.88 (dd, 1H, J=8.8, 2.4), 7.64 (d, 1H, J=2.4), 7.22-7.28 (m, 2H), 6.85-6.90 (m, 2H), 6.51 (d, 1H, J=9.0), 5.31 (broad s, 1H), 4.38 (d, 2H, J=5.4), 3.93 (s, 3H), 3.82 (s, 3H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-05215d3a28184519b2eafc0aae7642db
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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