Hexane → HCID 68818165, compound

HRID 735223Notes

Reaction equation

HRID 735223 reaction equation
[C:1]1([CH:7](C)[C:8](O)=[O:9])C=CC=CC=1.O=S(Cl)Cl.[CH3:16][O:17][C:18](=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH2:25].[CH3:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>CCOC(C)=O>[CH3:16][O:17][C:18](=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]([C:29]1[CH:28]=[CH:27][CH:32]=[CH:31][CH:30]=1)[C:8](=[O:9])[CH2:7][CH3:1]

Participants

6

Reactant 4

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

Product 1

HCID 68818165HCID 68818165, 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-phenyl-propionic acid (2.00 g, 13.3 mmol), SOCl2 (2.88 mL, 40.0 mmol) and 2-amino benzoic acid methyl ester (1.40 g, 9.31 mmol). After normal workup, the pure objective compound (2.50 g, 95%) was obtained as a pale yellow syrup by a flash column chromatography (n-hexane:EtOAc=20:1): 1H NMR (200 MHz, CDCl3) 51.60 (d, J=6.92 Hz, 3H, COCHCH3), 3.72-3.87 (m, 4H, OCH3, CH), 7.07 (td, J=6.10 Hz, 1.22 Hz, 1H, ArH), 7.23-7.55 (m, 6H, ArH), 7.95 (dd, J=7.73 Hz, 1.63 Hz, 1H, ArH), 8.69 (dd, J=8.55 Hz, 1.22 Hz, 1H, ArH).

Sources & evidence

ORD record
ord-936479276a934129b67dc41f533e82a8
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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