Ethanol, 1-ethoxy-2,2,2-trifluoro- → HCID 21094333, compound

HRID 990947Notes

Reaction equation

HRID 990947 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].C(O[CH:15](O)[C:16]([F:19])([F:18])[F:17])C.[BH3-]C#N.[Na+]>FC(F)(F)C(O)=O>[F:17][C:16]([F:19])([F:18])[CH2:15][NH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11]

Participants

5

Reactant 3

HCID 9897Ethanol, 1-ethoxy-2,2,2-trifluoro-HCID 49847212-Amino-5-NitrophenolHCID 5003444Sodium cyanoborohydride

Product 1

HCID 21094333HCID 21094333, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

This compound was prepared by General Method 7 (EXAMPLE 5) from 2-amino-5-nitrophenol (5.0 g, 32 mmol), 2,2,2-trifluoroacetaldehyde ethyl hemiacetal (9.4 g, 65 mmol) and NaBH3CN (4.1 g, 65 mmol) in 90 mL trifluoroacetic acid to afford 5.5 g (72%) of 2-(trifluoroethyl)amino-5-nitrophenol, a yellow solid, after flash chromatography (3:1 hexanes:EtOAc). Data for 2-(trifluoroethyl)amino-5-nitrophenol: 1H NMR (400 MHz, acetone-d6) 9.48 (broad s, 1H), 7.79 (dd, 1H, J=9.1, 2.4), 7.67 (d, 1H, J=2.4), 6.96 (d, 1H, J=8.8), 6.20 (broad s, 1H), 4.26-4.18 (m, 2H).

Sources & evidence

ORD record
ord-59faa8e389ec4501939e90d91a90377e
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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