Acetic Acid → HCID 178436143, compound

HRID 632504Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[CH:10]=[CH:11]/[C:12](=O)[CH2:13][C:14](=O)/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[CH:19][CH:18]=3)[CH:8]=2)[CH:3]=[CH:2]1.CC(O)=O.O.[NH2:39][NH2:40].C([O-])([O-])=O.[K+].[K+]>C1COCC1.CCOC(C)=O.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[CH:10]=[CH:11]/[C:12]3[NH:40][N:39]=[C:14](/[CH:15]=[CH:16]/[C:17]4[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)=[CH:19][CH:18]=4)[CH:13]=3)[CH:8]=2)[CH:3]=[CH:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

To 1.5 g of (1E,6E)-1-(1H-indol-6-yl)-7-[4-(2-morpholinoethoxy)phenyl]hepta-1,6-diene-3,5-dione were added 13.5 mL of AcOH and 1.31 mL of hydrazine monohydrate, and the mixture was stirred at 60° C. for 3 hours. The reaction mixture was allowed to cool back to room temperature and poured into a stirring mixture of 18.7 g of K2CO3, 95 mL of cold water, 30 mL of AcOEt and 20 mL of THF. The organic layer was separated, washed with saturated brine, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography (CHCl3/acetone or CHCl3/methanol system) to give 0.62 g of the title compound (42% yield).

Workup

temperatureto cool back to room temperature
customThe organic layer was separated
washwashed with saturated brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (CHCl3/acetone or CHCl3/methanol system)

Sources & evidence

ORD record: ord-890908d3078b4f77a83c9236b91eea24
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321752B2

Reaction notes

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