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

HRID 981937Notes

Reaction equation

HRID 981937 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]([CH2:24][CH3:25])[C:19](OCC)=[O:20].CC(C)([O-])C.[K+].[Cl-].[NH4+]>O1CCCC1>[CH2:24]([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)[CH3:25]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 67757092Ethyl alpha-[(9-amino-1,2,3,4-tetrahydroacridin-8-yl)oxy]butyrate hydrate

Product 1

HCID 537311453-Ethyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-oneYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl α-[(9-amino-1,2,3,4-tetrahydroacridin-8-yl)oxy]butyrate hydrate (30.34 g) in dry tetrahydrofuran (370 ml) was added potassium t-butoxide (13 g). The reaction mixture was stirred at room temperature for 1.5 hrs. Saturated ammonium chloride solution (150 ml) was added and stirring was continued for one hr. The mixture was concentrated and the concentrate was cooled. The solid was collected, washed with water, and dried to yield 21.26 g (78%) of product, mp 182°-183° C.

Workup

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

Sources & evidence

ORD record
ord-3d2eb93041a04184b7cb9eeb9df45db4
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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