Methanol → HCID 178484632, compound

HRID 632510Notes

Reaction equation

[CH3:1][N:2]([CH3:37])[C:3](=[O:36])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14](=O)[CH2:15][C:16](=O)/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:21][CH:20]=2)=[CH:8][CH:7]=1.Cl.Cl.[NH2:40][NH2:41].CO.C([O-])(O)=O.[Na+]>CCOC(C)=O>[CH3:1][N:2]([CH3:37])[C:3](=[O:36])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]2[NH:41][N:40]=[C:16](/[CH:17]=[CH:18]/[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:21][CH:20]=3)[CH:15]=2)=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To 2.70 g of N,N-dimethyl-2-[4-[(1E,6E)-7-[4-(2-morpholinoethoxy)phenyl]-3,5-dioxo-hepta-1,6-dienyl]phenoxy]acetamide were added 2.80 g of hydrazine dihydrochloride and 54 mL of methanol, and the mixture was stirred at 40° C. overnight. The reaction mixture was allowed to stand to cool, and poured into 200 mL of a saturated aqueous NaHCO3 solution. To this, 600 mL of AcOEt was added, and the organic layer was separated. The obtained organic layer was washed with saturated brine, dried over Na2SO4, and concentrated. The residue was purified by silica gel column chromatography (CHCl3/methanol system) to give 1.76 g of the title compound (66% yield).

Workup

temperatureto cool
customthe organic layer was separated
washThe obtained organic layer was washed with saturated brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (CHCl3/methanol system)

Sources & evidence

ORD record: ord-cb001363f10641adbf9801827d44d198
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321752B2

Reaction notes

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