Hexane → 4,6-Dibromo-2-[2-(4-methoxy-3-nitro-phenyl)-propionylamino]-benzoic acid methyl ester

HRID 735234Notes

Reaction equation

HRID 735234 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10]([OH:12])=O)=[CH:5][C:4]=1[N+:14]([O-:16])=[O:15].O=S(Cl)Cl.[CH3:21][O:22][C:23](=[O:33])[C:24]1[C:29]([Br:30])=[CH:28][C:27]([Br:31])=[CH:26][C:25]=1[NH2:32].CCCCCC>CCOC(C)=O>[CH3:21][O:22][C:23](=[O:33])[C:24]1[C:29]([Br:30])=[CH:28][C:27]([Br:31])=[CH:26][C:25]=1[NH:32][C:10](=[O:12])[CH:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([N+:14]([O-:16])=[O:15])[CH:5]=1)[CH3:13]

Participants

6

Reactant 4

HCID 8058HexaneHCID 24386Thionyl ChlorideHCID 214441642-(4-Methoxy-3-nitrophenyl)propanoic acidHCID 68817243Methyl 2-amino-4,6-dibromobenzoate

Product 1

HCID 688177454,6-Dibromo-2-[2-(4-methoxy-3-nitro-phenyl)-propionylamino]-benzoic acid methyl esterYield 59.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The objective compound was prepared by the same procedure for the intermediate 1, using a 2-(4-methoxy-3-nitro-phenyl)-propionic acid (0.22 g, 0.98 mmol), SOCl2 (0.35 mL, 0.49 mmol), and 2-amino-4,6-dibromo-benzoic acid methyl ester (0.15 g, 0.49 mmol). After normal workup, the pure objective compound (0.15 g, 59%) was obtained as pale yellow solid by a flash column chromatography (n-hexane:EtOAc=3:1): 1H NMR (200 MHz, DMSO-d6) δ 1.39 (d, J=6.8 Hz, 3H, CH3), 3.55 (s, 3H, OCH3), 3.88 (s, 3H, CO2CH3), 3.89 (m, 1H, CH), 7.32 (d, J=9.0 Hz, 1H, ArH), 7.63 (dd, J=8.8, 1.8 Hz, 1H, ArH), 7.80-7.84 (m, 2H, ArH), 8.13-8.15 (m, 1H, ArH).

Sources & evidence

ORD record
ord-08e44f9df01a41b2a7ff835789eb8269
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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