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

HRID 981941Notes

Reaction equation

HRID 981941 reaction equation
[OH2:1].[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]=2C(C1C=CC=CC=1)C(O)=O.[CH3:27][C:28](C)([O-:30])[CH3:29].[K+].[Cl-].[NH4+]>O1CCCC1>[C:27]1([CH:28]2[C:29](=[O:1])[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:30]2)[CH2:12][CH2:13][CH2:14][CH2:15]4)[CH:5]=[CH:4][CH:3]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 86744620HCID 86744620, compound

Product 1

HCID 545386111,3,9,10,11,12-Hexahydro-3-phenyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-oneYield 148.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl α-[(9-amino-1,2,3,4-tetrahydroacridin-8-yl]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° (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-687232ce29694398abaee04541c24a14
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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