Propanal → 2-Methoxy-N-2,2,2-trifluoroethyl-4-nitroaniline

HRID 413317

Reaction equation

HRID 413317 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].O.[F:14][C:15]([F:19])([F:18])[CH:16]=O.C(=O)CC>>[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][CH2:16][C:15]([F:19])([F:18])[F:14]

Participants

4

Reactant 3

HCID 527PropanalHCID 73372-Methoxy-4-nitroanilineHCID 27813662,2,2-Trifluoroacetaldehyde hydrate

Product 1

HCID 222793132-Methoxy-N-2,2,2-trifluoroethyl-4-nitroaniline

Procedure

This compound was prepared in a similar fashion as that described in Example 2, General Procedure IV but using 2-amino-5-nitroanisole and trifluoroacetaldehyde hydrate in place of Compound 200 and propionaldehyde. Compound 465 was isolated as a light brown crystalline solid after recrystallization (1:1 EtOAc:hexanes, 30 mL): Rf 0.52 (2:1 hexanes:EtOAc); 1H NMR (400 MHz, acetone-d6) 7.87 (dd, J=8.9, 2.4, 1H), 7.69 (d, J=2.4, 1H), 6.96 (d, J=8.9, 1H), 6.38 (broad s, 1H), 4.20 (qd, J=9.3, 7.1, 2H), 4.00 (s, 3H).

Workup

  1. customThis compound was prepared in a similar fashion as

Sources & evidence

ORD record
ord-e2c0b71aa55a4091bde027f82e09e312
Source dataset
uspto-grants-2003_05
Patent number
US06566372B1

Linked notes

Loading…