Sodium Methoxide → 3-Amino-2,3,4,5-tetrahydro-1H-benzazepin-2-one

HRID 647850Notes

Reaction equation

HRID 647850 reaction equation
[NH2:1][CH:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16])[C:3](OCC)=[O:4].C[O-].[Na+]>CO>[NH2:1][CH:2]1[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:3]1=[O:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 20244742HCID 20244742, compound

Product 1

HCID 44344333-Amino-2,3,4,5-tetrahydro-1H-benzazepin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of ethyl 2-amino-4-(2-aminophenyl)butyrate (35.0 g) in methanol (100 ml) was added to a solution of sodium methoxide in methanol [prepared from sodium (1.0 g) and methanol (400 ml)] with stirring, under a nitrogen atmosphere. The reaction mixture was refluxed for 65 hours and evaporated under reduced pressure. The residue was distributed between water (100 ml) and dichloromethane (400 ml). The aqueous solution was extracted with dichloromethane (400 ml), and the combined organic solutions washed with water (100 ml) and dried over magnesium sulfate. Evaporation to dryness and trituration with ether (250 ml) gave 3-amino-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one, m.p. 161°-162° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 65 hours
  2. customevaporated under reduced pressure
  3. extractionThe aqueous solution was extracted with dichloromethane (400 ml)
  4. washthe combined organic solutions washed with water (100 ml)
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation to dryness and trituration with ether (250 ml)

Sources & evidence

ORD record
ord-676ca1f907fd430f960a352386b77d98
Source dataset
uspto-grants-1983_10
Patent number
US04410520

Reaction notes

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