Ammonium Hydroxide → 5-(4-Chlorophenyl)-10-methyl-7H-isoxazolo[5,4-c]pyrido[2,3-e]azepin-2-amine

HRID 2401407Notes

Reaction equation

HRID 2401407 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)=[N:10][CH2:9][C:8]3[O:19][N:20]=[C:21]([CH3:22])[C:7]=3[C:6]=2[N:23]=1.[OH-].[NH4+:25].[Cl-].[NH4+]>CCO>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]2[C:5]3[CH:4]=[CH:3][C:2]([NH2:25])=[N:23][C:6]=3[C:7]3[C:21]([CH3:22])=[N:20][O:19][C:8]=3[CH2:9][N:10]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 573889332-Chloro-5-(4-chlorophenyl)-10-methyl-7H-isoxazolo[5,4-c]pyrido[2,3-e]azepine

Product 1

HCID 678147955-(4-Chlorophenyl)-10-methyl-7H-isoxazolo[5,4-c]pyrido[2,3-e]azepin-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-chloro-5-(4-chlorophenyl)-10-methyl-7H-isoxazolo[5,4-c]pyrido[2,3-e]azepine (0.050 g, 0.145 mmol) in EtOH (1 mL) was added concentrated ammonium hydroxide (4.00 mL) and ammonium chloride (just enough to saturate the reaction) at room temperature. The reaction was heated to 100° C. overnight before the desired product was extracted using CH2Cl2 (repeated 4 times). The organic layers were combined, dried over Na2SO4 and concentrated to dryness. The residue was purified by flash chromatography (hexane/EtOAc 6:4 to 0:10) to give the title compound as a tan solid (0.008 g). LC/MS m/z 325 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 7.43 (td, J=2.10, 8.70 Hz, 2H), 7.37 (td, J=2.10, 8.70 Hz, 2H), 7.24 (d, J=8.72 Hz, 1H), 6.77 (br. s, 2H), 6.38 (d, J=8.72 Hz, 1H), 4.61 (s, 2H), 2.56 (s, 3H).

Workup

  1. concentrationto saturate
  2. customthe reaction) at room temperature

Sources & evidence

ORD record
ord-945bb85bcab44a6699a8890994fabbfb
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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