Water → HCID 391101, compound

HRID 1683877Notes

Reaction equation

HRID 1683877 reaction equation
[CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[CH:5]1[CH2:19][C:9]2=[CH:10][CH:11]=[C:12]3[C:16]([NH:15][C:14](=O)[C:13]3=O)=[C:8]2[CH2:7][CH2:6]1)[CH2:2][CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[CH2:20]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:19][C:9]2=[CH:10][CH:11]=[C:12]3[C:16]([NH:15][CH:14]=[CH:13]3)=[C:8]2[CH2:7][CH2:6]1)[CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19041527HCID 19041527, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 391101HCID 391101, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 7-di-n-propylamino-6,7,8,9-tetrahydro-1H-benzo[g]indole-2,3-dione, 2a, (Chart 1) (22.0 g, 73.2 mmol) in dry diethyl ether (100 mL) was added dropwise to a suspension of lithiumaluminum hydride (9.0 g, 237 mmol) in dry diethyl ether (600 mL). After stirring overnight at ambient temperature, water (9.0 mL), 15% sodium hydroxide (9 mL) and water (27 mL) were consecutively added. The mixture was stirred for 20 minutes followed by filtration of inorganic material. The solution was dried (sodium sulfate), filtered and evaporated to yield 17 g of a blue off, which was purified on silica (acetone/methanol, 20:1) to yield 7.4 g (37%) of the pure material. For analytical and biological purposes, the fumarate salt (1/2 fum) was prepared which was recrystallized from ethanol/diethyl ether. m.p. 201°-205° C.

Workup

  1. stirringThe mixture was stirred for 20 minutes
  2. filtrationfollowed by filtration of inorganic material
  3. dry with materialThe solution was dried (sodium sulfate)
  4. filtrationfiltered
  5. customevaporated
  6. customto yield 17 g of a blue off, which
  7. customwas purified on silica (acetone/methanol, 20:1)

Sources & evidence

ORD record
ord-1dbfd13314bb4d2cbcb8167c94d2a5cb
Source dataset
uspto-grants-1997_06
Patent number
US05639778

Reaction notes

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