Hexane → HCID 68815664, compound

HRID 735235Notes

Reaction equation

HRID 735235 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=O)=[CH:4][C:3]=1[O:13][CH3:14].O=S(Cl)Cl.[CH3:19][O:20][C:21](=[O:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH2:28].CCCCCC>CCOC(C)=O>[CH3:19][O:20][C:21](=[O:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][C:9](=[O:11])[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([O:13][CH3:14])[CH:4]=1)[CH3:12]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8635Methyl AnthranilateHCID 24386Thionyl ChlorideHCID 189870744-Hydroxy-3-methoxy-α-methylbenzeneacetic acid

Product 1

HCID 68815664HCID 68815664, compoundYield 83.7%

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-hydroxy-3-methoxy-phenyl)-propionic acid (1.08 g, 5.50 mmol), SOCl2 (1.20 mL, 16.6 mmol), and 2-amino-benzoic acid methyl ester (0.56 g, 3.7 mmol). After normal workup, the pure objective compound (1.02 g, 56%) was obtained as pale yellow syrup by a flash column chromatography (n-hexane:EtOAc=10:1): 1H NMR (200 MHz, CDCl3) δ 1.57 (d, J=7.32 Hz, 3H, CH3), 3.72 (q, J=7.32 Hz, 1H, CH), 3.85 (s, 3H, OCH3), 3.88 (s, 3H, COOCH3), 5.73 (br s, 1H, ArOH), 6.89-7.05 (m, 4H, ArH), 7.45 (t, J=8.55 Hz, 1H, ArH), 7.94 (d, J=7.73 Hz, 1H, ArH), 8.67 (d, J=8.55 Hz, 1H, ArH), 11.07 (br s, 1H, NH).

Sources & evidence

ORD record
ord-de1be6373dba4aa88084287ff3fdc4e1
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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