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

HRID 1195784Notes

Reaction equation

HRID 1195784 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]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:19]([O:21]C)=O.CC(C)([O-])C.[K+].[Cl-].[NH4+]>O1CCCC1>[C:23]1([CH:18]2[C:19](=[O:21])[NH:2][C:3]3=[C:16]4[C:11](=[N:10][C:9]5=[CH:8][CH:7]=[CH:6][C:5](=[C:4]35)[O:17]2)[CH2:12][CH2:13][CH2:14][CH2:15]4)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 67755922HCID 67755922, compound

Product 1

HCID 545386111,3,9,10,11,12-Hexahydro-3-phenyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-oneYield 80.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl α-[(9-amino-1,2,3,4-tetrahydroacridin-8-yl)oxy]phenylacetate hydrate (5.26 g) was dissolved dry tetrahydrofuran (100 ml) and potassium tert-butoxide (1.70 g) was added. After stirring for 1 hr, saturated ammonium chloride solution (100 ml) was added, and stirring was continued for 30 min. The reaction mixture was evaporated and the solid was collected and washed with water. Recrystallization from dimethylformamide-water gave 3.69 g (77.0%) of product, mp 250° C. (dec).

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for 30 min
  4. customThe reaction mixture was evaporated
  5. customthe solid was collected
  6. washwashed with water
  7. customRecrystallization from dimethylformamide-water

Sources & evidence

ORD record
ord-b93919a66cd542c7b0a572f69899b06a
Source dataset
uspto-grants-1992_05
Patent number
US05112829

Reaction notes

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