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

HRID 26401

Reaction equation

HRID 26401 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]

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 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-16a17a0b36e14ed6b91cdc45dfc700a2
Source dataset
uspto-grants-1979_04
Patent number
US04150032

Linked notes

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