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3-(3,4-Dimethoxyphenyl)-1-oxo-3,3a,4,5,6,7-hexahydro-2H-1lambda~5~-indole → HCID 21500388, compound

HRID 1729710
Notes
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Reaction equation

HRID 1729710 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:19]2[CH:27]3[C:22]([CH2:23][CH2:24][CH2:25][CH2:26]3)=[N+:21]([O-:28])[CH2:20]2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]>CCOCC.O1CCCC1>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:19]2[CH:27]3[C:22]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)([CH2:23][CH2:24][CH2:25][CH2:26]3)[N:21]([OH:28])[CH2:20]2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 215003863-(3,4-Dimethoxyphenyl)-1-oxo-3,3a,4,5,6,7-hexahydro-2H-1lambda~5~-indoleHCID 178418255HCID 178418255, compound

Product 1

HCID 21500388HCID 21500388, compoundYield 23.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
35 °C

Procedure

A volume of 75 ml of 3 M phenylmagnesium bromide in ether was added over a period of five minutes to a warm (35° C) stirred solution of 41.25 g (0.015 mole) of 3,3a,4,5,6,7-hexahydro-3-(3,4-dimethoxyphenyl)-2H-indole-1-oxide in 500 ml of tetrahydrofuran. After stirring for 2 hours at room temperature, most of the THF was distilled off at atmospheric pressure. Ice water (1 liter) was added and the paste-like solid was filtered. The damp filter cake was added to 500 ml of 1N HCl. The taffy-like material which remained out of solution was added to 10 MKOH (300 ml). The mixture was extracted into 1.5 l methylenechloride and the extract was dried (K2CO3), charcoaled, filtered and concentrated. The residue was dissolved in 200 ml of petroleum ether. There was obtained 12.5 g (23.6%) of a white solid melting at 166°-168° C. Recrystallization from 2-propanol gave pure material melting at 168°-170° C.

Workup

  1. distillationwas distilled off at atmospheric pressure
  2. additionIce water (1 liter) was added
  3. filtrationthe paste-like solid was filtered
  4. additionThe damp filter cake was added to 500 ml of 1N HCl
  5. additionwas added to 10 MKOH (300 ml)
  6. extractionThe mixture was extracted into 1.5 l methylenechloride
  7. dry with materialthe extract was dried (K2CO3)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. dissolutionThe residue was dissolved in 200 ml of petroleum ether

Sources & evidence

ORD record
ord-11c1e92350e64264b7f8cc5c698860de
Source dataset
uspto-grants-1976_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03989714

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes