Hexane → HCID 68815880, compound

HRID 735233Notes

Reaction equation

HRID 735233 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:14])[C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].O=S(Cl)Cl.[CH3:19][O:20][C:21](=[O:30])[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[NH2:29].CCCCCC>CCOC(C)=O>[CH3:19][O:20][C:21](=[O:30])[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[NH:29][C:11](=[O:13])[CH:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[CH3:14]

Participants

6

Reactant 4

HCID 8058HexaneHCID 24386Thionyl ChlorideHCID 80001Methyl 4-chloroanthranilateHCID 892442-(4-Nitrophenyl)propionic acid

Product 1

HCID 68815880HCID 68815880, compoundYield 95%

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-nitro-phenyl)-propionic acid (1.95 g, 10.0 mmol), SOCl2 (3.6 mL, 33.4 mmol), and 2-amino-4-chloro-benzoic acid methyl ester (1.24 g, 6.67 mmol). After normal workup, the pure objective compound (2.29 g, 95%) was obtained as slightly yellow solid by a flash column chromatography (n-hexane:EtOAc=8:1): 1H NMR (200 MHz, CDCl3) δ 1.65 (d, J=7.3 Hz, 3H, CH3), 3.83-3.93 (m, 4H, CO2CH3 & CH), 7.04 (dd, J=8.5, 2.0 Hz, 1H, ArH), 7.58 (d, J=8.9 Hz, 2H, ArH), 7.93 (d, J=8.5 Hz, 1H, ArH), 8.21 (d, J=8.9 Hz, 2H, ArH), 8.79 (d, J=2.0 Hz, 1H, ArH), 11.09 (br s, 1H, NH).

Sources & evidence

ORD record
ord-0db995ccbf7a4c44b75d018cf0e45892
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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