(3R)-3-ethyl-7-fluoro-4-(4-hydroxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-one → (3R)-1benzyl-3-ethyl-7-fluoro-4-(3-hydroxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

HRID 898220Notes

Reaction equation

HRID 898220 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=2)[N:11]([C:19](=[O:28])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26]C)[CH:21]=2)[C@H:10]([CH2:29][CH3:30])[C:9]1=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([C@H]1N(C(=O)C2C=CC(O)=CC=2)C2C(=CC(F)=CC=2)N(C)C1=O)C>>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=2)[N:11]([C:19](=[O:28])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=2)[C@H:10]([CH2:29][CH3:30])[C:9]1=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 11709655(3R)-3-ethyl-7-fluoro-4-(4-hydroxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-oneHCID 69221455(3R)-1-benzyl-3-ethyl-7-fluoro-4-(3-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

Product 1

HCID 11516990(3R)-1benzyl-3-ethyl-7-fluoro-4-(3-hydroxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-oneYield 74%

Procedure

(3R)-1-Benzyl-3-ethyl-7-fluoro-4-(3-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one was treated according to the procedure for the preparation of (3R)-3-ethyl-7-fluoro-4-(4-hydroxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-one (see Example 1) to yield (3R)-1benzyl-3-ethyl-7-fluoro-4-(3-hydroxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (74%). [α]D25=−279° (c=0.0095G/ML, CHCl3); MS (ESI) m/z 405 ([M+H]+); MS (ESI) m/z 403 ([M−H]−); HRMS: calcd for C24H21FN2O3.0.25H2O, 408.6563; found (ESI+), 405.16003; Anal. Calcd for C24H21FN2O3.0.25H2O: C, 70.49; H, 5.30; N, 6.85. Found: C, 70.42; H, 5.19; N, 6.75.

Sources & evidence

ORD record
ord-1c132960311f467ca65c9d055094388a
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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