Water → HCID 13491594, compound

HRID 1284919Notes

Reaction equation

HRID 1284919 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][N:8]1[CH2:22][CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:11]2=[CH:12][CH:13]=[C:14]3[C:18]([NH:17][C:16](=O)[C:15]3=O)=[C:10]2[CH2:9]1.O>C(OCC)C.O1CCCC1>[CH3:7][N:8]1[CH2:22][CH:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:11]2=[CH:12][CH:13]=[C:14]3[C:18]([NH:17][CH:16]=[CH:15]3)=[C:10]2[CH2:9]1

Participants

6

Reactant 3

HCID 962WaterHCID 13491592HCID 13491592, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13491594HCID 13491594, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

20 g (0.524 mol) of LiAlH4 are suspended in 400 ml of absolute diethyl ether at room temperature, with stirring, while flushing with nitrogen and in the absence of moisture. 550 ml of absolute tetrahydrofuran are then added, followed by 34 g (0.116 mol) of 8-methyl-6-phenyl-6,7,8,9-tetrahydro-1H-pyrido[4,3-g]indole-2,3-dione in portions. The reaction mixture is subsequently stirred at room temperature for 31/2 hours. To dissociate the reaction complex, a solution of 42 ml of H2O in 160 ml of tetrahydrofuran is added dropwise, with cooling. The inorganic solid is filtered off and the filtrate is freed from the solvent on a rotary evaporator. The residue is chromatographed on silica gel 60 with an eluent mixture of: ethyl acetate and 8.3% of MeOH. The pure substance is dried in a desiccator over P2O5 at 60° C. under a water pump vacuum.

Workup

  1. customwhile flushing with nitrogen and in the absence of moisture
  2. addition550 ml of absolute tetrahydrofuran are then added
  3. stirringThe reaction mixture is subsequently stirred at room temperature for 31/2 hours
  4. temperaturewith cooling
  5. filtrationThe inorganic solid is filtered off
  6. customthe filtrate is freed from the solvent on a rotary evaporator
  7. customThe residue is chromatographed on silica gel 60 with an eluent mixture of: ethyl acetate and 8.3% of MeOH
  8. dry with materialThe pure substance is dried in a desiccator over P2O5 at 60° C. under a water pump vacuum

Sources & evidence

ORD record
ord-36b7d3799b014c9996ba6a0949685f06
Source dataset
uspto-grants-1986_01
Patent number
US04564613

Reaction notes

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