Hexane → HCID 68818273, compound

HRID 735224Notes

Reaction equation

HRID 735224 reaction equation
[C:1]1([CH:7]([CH3:11])[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=S(Cl)[Cl:14].[CH3:16][O:17][C:18](=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH2:25].CCCCCC>CCOC(C)=O>[CH3:16][O:17][C:18](=[O:26])[C:19]1[CH:24]=[CH:23][C:22]([Cl:14])=[CH:21][C:20]=1[NH:25][C:8](=[O:10])[CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH3:11]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8635Methyl AnthranilateHCID 102962-Phenylpropionic acidHCID 24386Thionyl Chloride

Product 1

HCID 68818273HCID 68818273, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The objective compound was prepared by the same procedure for the intermediate 1, using a 2-phenyl-propionic acid (2.00 g, 13.3 mmol), SOCl2 (2.88 mL, 40.0 mmol) and 2-amino benzoic acid methyl ester (1.72 g, 9.31 mmol). After normal workup, the pure objective compound (2.43 g, 82%) was obtained as a pale yellow syrup by a flash column chromatography (n-hexane:EtOAc=20:1): 1H-NMR (200 MHz, CDCl3) δ 1.61 (d, J=6.92 Hz, 3H, CH3), 3.72-3.85 (m, 4H, OCH3, CH), 6.95 (d, J=2.03 Hz, 1H, ArH), 6.99 (d, J=2.03 Hz, 1H, ArH), 7.24-7.45 (m, 5H, ArH), 7.84 (d, J=8.55 Hz, 1H, ArH), 8.84 (d, J=2.03 Hz, 1H, ArH), 11.15 (br s, 1H, NH).

Sources & evidence

ORD record
ord-2fef78d37734428e84d7e201c4c94849
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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