Ethanol → HCID 54330103, compound

HRID 1763659Notes

Reaction equation

HRID 1763659 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]2[CH2:6][CH2:7][N:8]3[CH:19]=[CH:18][CH:17]=[C:9]3[C:10](=[CH:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])[C:4]=2[CH:3]=1.[CH:22](OCC)(OCC)OCC.C(O)C.[BH4-].[Na+]>C(OCC)(=O)C>[CH3:22][NH:1][C:2]1[CH:21]=[CH:20][C:5]2[CH2:6][CH2:7][N:8]3[CH:19]=[CH:18][CH:17]=[C:9]3[C:10](=[CH:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 31214Ethyl orthoformateHCID 4311764Sodium borohydrideHCID 54400122HCID 54400122, compound

Product 1

HCID 54330103HCID 54330103, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 9-amino-11-(3-dimethylaminopropylidene)-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepine in triethyl orthoformate (2.8 g.; 10 mmoles in 80 ml.) was refluxed for 5 hours. The volatiles were removed under vacuum and the residue dissolved in 100 ml. of absolute ethanol was stirred in an ice bath as sodium borohydride (0.88 g., 0.024 moles) was added over a period of 10 minutes. The mixture was stirred for a period of 2 hours. After concentration of the ethanol, the residue was dissolved in ethyl acetate, washed with water, dried over Na2SO4 and concentrated to dryness to yield 9-methylamino-11-(3-dimethylaminopropylidene)-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepine.

Workup

  1. customThe volatiles were removed under vacuum
  2. dissolutionthe residue dissolved in 100 ml
  3. additionwas 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-576f886ce1c74257927d852ad918d518
Source dataset
uspto-grants-1978_09
Patent number
US04112112

Reaction notes

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