Tetrahydrofuran → HCID 13477799, compound

HRID 371079Notes

Reaction equation

HRID 371079 reaction equation
[CH:1]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:2]=1[CH:3]=[C:4]1[N:10]2[CH2:9][C:8]2[CH:15]=[CH:16][CH:17]=[CH:18][C:7]=2[NH:6][C:5]1=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[OH-].[Na+]>O>[CH:1]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:2]=1[CH:3]=[C:4]1[N:10]2[CH2:9][C:8]2[CH:15]=[CH:16][CH:17]=[CH:18][C:7]=2[NH:6][CH2:5]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 13477797HCID 13477797, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13477799HCID 13477799, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 7.1 g (0.0286 mole) of 6H-indolo[2,1-c][1,4]benzodiazepin-12(11H)-one, the product of Example 1, 2.17 g (0.057 mole) of LAH and 100 ml of THF was refluxed for 5 hours under a nitrogen atmosphere. The reaction mixture was cooled to room temperature followed by the addition of 2.1 ml of water, 2.1 ml of 15% NaOH solution and 6.3 ml of water. The white solid obtained after 0.5 hour was filtered to give a light yellow filtrate which was concentrated in vacuo to give 6.54 g of off-white solid. Recrystallization from i-PrOH/EtOAc gave the title compound as a white solid, mp 176°-177° C.

Workup

  1. customThe white solid obtained after 0.5 hour
  2. filtrationwas filtered
  3. customto give a light yellow filtrate which
  4. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-d3fde8a3045a4423908a1cad9d98510b
Source dataset
uspto-grants-1985_07
Patent number
US04529724

Reaction notes

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