Ethanol → HCID 20310667, compound

HRID 1438726Notes

Reaction equation

HRID 1438726 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]2[CH:6]=[CH: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[CH:6]=[CH: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 20310593HCID 20310593, compound

Product 1

HCID 20310667HCID 20310667, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 9-amino-11H-pyrrolo[2,1-b] [3]-benzazepin-11-one in triethyl orthoformate (2.17 g., 10 mmoles in 80 ml.) is refluxed for 5 hrs. The volatiles are removed under vacuum and the residue, dissolved in 100 ml. 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 hrs. 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-11H-pyrrolo[2,1-b] [3]benzazepin-11-one as a brown amorphous solid.

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-a9273035a13145faa457f3d701f03ea6
Source dataset
uspto-grants-1977_11
Patent number
US04056536

Reaction notes

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