Ethanol → HCID 20310625, compound

HRID 1763634Notes

Reaction equation

HRID 1763634 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]2[CH2:6][CH2:7][N:8]3[CH:14]=[CH:13][CH:12]=[C:9]3[C:10](=[O:11])[C:4]=2[CH:3]=1.[CH:17](OCC)(OCC)OCC.C(O)C.[BH4-].[Na+]>C(OCC)(=O)C>[CH3:17][NH:1][C:2]1[CH:16]=[CH:15][C:5]2[CH2:6][CH2:7][N:8]3[CH:14]=[CH:13][CH:12]=[C:9]3[C:10](=[O:11])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 31214Ethyl orthoformateHCID 4311764Sodium borohydrideHCID 13152894HCID 13152894, compound

Product 1

HCID 20310625HCID 20310625, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 9-amino-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one in triethyl orthoformate (2.14 g.; 10 mmoles in 80 ml) is refluxed for 5 hours. The volatiles are removed under vacuum and the residue dissolved in 100 ml. of absolute ethanol is stirred in an ice bath as sodium borohydride (0.88 g.; 0.024 moles) is added over a period of 10 minutes. The mixture is stirred for a period of 2 hours. After concentration of the ethanol, the residue is dissolved in ethyl acetate, washed with water, dried over Na2SO4 and concentrated to dryness to yield 9-methylamino-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.

Workup

  1. customThe volatiles are removed under vacuum
  2. dissolutionthe residue dissolved in 100 ml
  3. additionis added over a period of 10 minutes
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-da41ebb876dc40cb9dd677809b775ef9
Source dataset
uspto-grants-1978_09
Patent number
US04112112

Reaction notes

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