(3R)-3-Ethyl-7-fluoro-3,4-dihydroquinoxalin-2(1H)-one → (3R)-3-ethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one

HRID 898227Notes

Reaction equation

HRID 898227 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([NH:8][C@H:9]([CH2:13][CH3:14])[C:10](O)=[O:11])[CH:7]=1.C([C@H]1NC2C(=CC(F)=CC=2)NC1=O)C>>[CH2:13]([C@H:9]1[NH:8][C:6]2[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:7]=2)[NH:15][C:10]1=[O:11])[CH3:14]

Participants

3

Reactant 2

HCID 69220784(3R)-3-Ethyl-7-fluoro-3,4-dihydroquinoxalin-2(1H)-oneHCID 69221394(R)-2-(5-fluoro-2-nitrophenylamino)-butyric acid

Product 1

HCID 69222176(3R)-3-ethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-oneYield 54%

Procedure

(2R)-2-(5-Fluoro-2-nitrophenylamino)-butyric acid was treated according to the procedure for the preparation of (3R)-3-ethyl-7-fluoro-3,4-dihydroquinoxalin-2(1H)-one (see Example 1) to yield (3R)-3-ethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one (54%). MS (ESI) m/z 195 ([M+H]+); HRMS: calcd for C10H11FN2O, 194.08558; found (ESI_FT), 195.08807; Anal. Calcd for C10H11FN2O: C, 61.85; H, 5.71; N, 14.42. Found: C, 61.77; H, 5.76; N, 14.33.

Sources & evidence

ORD record
ord-199eb6c28bf1473ca3721f728faedd35
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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