Ammonium Chloride → 1,3,9,10,11,12-Hexahydro-3-methyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one

HRID 981929Notes

Reaction equation

HRID 981929 reaction equation
O.[NH2:2][C:3]1[C:4]2[C:9]([N:10]=[C:11]3[C:16]=1[CH2:15][CH2:14][CH2:13][CH2:12]3)=[CH:8][CH:7]=[CH:6][C:5]=2[O:17][CH:18]([CH3:23])[C:19](OC)=[O:20].CC(C)([O-])C.[K+].[Cl-].[NH4+]>O1CCCC1>[CH3:23][CH:18]1[C:19](=[O:20])[NH:2][C:3]2=[C:16]3[C:11](=[N:10][C:9]4=[CH:8][CH:7]=[CH:6][C:5](=[C:4]24)[O:17]1)[CH2:12][CH2:13][CH2:14][CH2:15]3

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 67756055Methyl alpha-[(9-amino-1,2,3,4-tetrahydroacridin-8-yl)oxy]propionate hydrate

Product 1

HCID 541566201,3,9,10,11,12-Hexahydro-3-methyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-oneYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the methyl α-[(9-amino-1,2,3,4-tetrahydroacridin-8-yl)oxy]propionate hydrate (3.7 g) in dry tetrahydrofuran (65 ml) was added potassium t-butoxide (1.62 g). The reaction mixture was stirred at room temperature for one hr, saturated ammonium chloride solution (18.2 ml) was added, and stirring was continued for one hr. The mixture was concentrated. The solution was cooled, the solid was collected, washed with water, and dried to yield 2.90 g (90%) of product, mp 200° C. (dec).

Workup

  1. stirringstirring
  2. waitwas continued for one hr
  3. concentrationThe mixture was concentrated
  4. temperatureThe solution was cooled
  5. customthe solid was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-16da12d9adf34164ad4d62a306f6b690
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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