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Diethyl Ether → 9b-Allyl-8-methoxy-3-methyl-5,9b-dihydrobenz[e]indoline

HRID 224969
Notes
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Reaction equation

HRID 224969 reaction equation
[CH2:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[CH:6]=[CH:5][C:4]=2[NH:3][CH2:2]1.[C:14]1(C([O-])=C([N+]([O-])=O)C=[C:19]([N+]([O-])=O)[CH:18]=1)[N+]([O-])=O.C1([C:44]([OH:45])=C([N+]([O-])=O)C=C([N+]([O-])=O)C=1)[N+]([O-])=O.[OH-].[Li+].[CH3:48]COCC>C(O)C>[CH2:19]([C:9]12[C:8]3[CH:10]=[C:11]([O:45][CH3:44])[CH:12]=[CH:13][C:7]=3[CH2:6][CH:5]=[C:4]1[N:3]([CH3:48])[CH2:2][CH2:1]2)[CH:18]=[CH2:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 3939Lithium HydroxideHCID 6954Picric AcidHCID 4432340Picrate3×HCID 111479652,3-Dihydro-1h-benzo[e]indole

Product 1

HCID 233307809b-Allyl-8-methoxy-3-methyl-5,9b-dihydrobenz[e]indoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The benz[e]indoline IIa was regenerated from the picrate XIVd (X=picric acid) as follows: A mixture of finely powder picrate (10 mmol), 1 N aqueous lithium hydroxide (50 ml), ethanol (20 ml) and ether (100 ml) in a separatory funnel was shaken until all the picrate had dissolved. The ether phase was washed with water and, after drying, was evaporated to dryness to give the free base IIa quantitatively.

Workup

  1. dissolutionhad dissolved
  2. washThe ether phase was washed with water
  3. customafter drying
  4. customwas evaporated to dryness
  5. customto give the free base IIa quantitatively

Sources & evidence

ORD record
ord-2a59832b8cf3466b9a85bdd208afeaee
Source dataset
uspto-grants-1980_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04234731

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes