1,3-Diethyl 2-(acetylamino)-2-[(4-bromo-2-nitrophenyl)methyl]propanedioate → HCID 59627195, compound

HRID 1926697Notes

Reaction equation

HRID 1926697 reaction equation
C([NH:4][C:5]([CH2:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([CH3:24])[C:18]=1[N+:25]([O-:27])=O)(C(OCC)=O)[C:6](OCC)=[O:7])(=O)C.C(NC(CC1C=CC(Br)=CC=1[N+]([O-])=O)(C(OCC)=O)C(OCC)=O)(=O)C.BrCC1C=C(Cl)C=C(C)C=1[N+]([O-])=O>>[NH2:4][CH:5]1[CH2:16][C:17]2[C:18](=[C:19]([CH3:24])[CH:20]=[C:21]([Cl:23])[CH:22]=2)[N:25]([OH:27])[C:6]1=[O:7]

Participants

4

Reactant 3

HCID 106225521,3-Diethyl 2-(acetylamino)-2-[(4-bromo-2-nitrophenyl)methyl]propanedioateHCID 59627070HCID 59627070, compoundHCID 59627186HCID 59627186, compound

Product 1

HCID 59627195HCID 59627195, compound

Procedure

Diethyl acetamido(5-chloro-3-methyl-2-nitrobenzyl)malonate (39) Following the procedure for the preparation of diethyl acetamido(4-bromo-2-nitrobenzyl)malonate (24) in Example 5,1-(bromomethyl)-5-chloro-3-methyl-2-nitrobenzene (38) was converted to the title product, which was obtained as a solid (65%). LCMS m/z 401.0 (M+1). 1H NMR (400 MHz, DMSO-d6) δ 1.15 (t, J=7.1 Hz, 6H), 1.90 (s, 3H), 2.24 (br s, 3H), 3.53 (s, 2H), 4.10-4.17 (m, 4H), 7.05 (br d, J=2.2 Hz, 1H), 7.56 (apparent dd, J=2.3, 0.7 Hz, 1H), 8.31 (br s, 1H).

Sources & evidence

ORD record
ord-a00c580d85434550b904cfe1d30e688f
Source dataset
uspto-grants-2012_05
Patent number
US08183238B2

Reaction notes

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