4-Toluenesulfonyl chloride → 8,9,10,11-Tetrahydro[1,2]oxazepino[2',3':1,2]imidazo[4,5-c]quinolin-6-amine

HRID 415513Notes

Reaction equation

HRID 415513 reaction equation
[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]1[N:14]3[O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:13]3=[N:12][C:4]=1[CH:5]=[N+:6]2[O-].[NH4+:20].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]1[N:14]3[O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:13]3=[N:12][C:4]=1[C:5]([NH2:20])=[N:6]2

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 666199128,9,10,11-Tetrahydro[1,2]oxazepino[2',3':1,2]imidazo[4,5-c]quinoline 5-oxide

Product 1

HCID 248520498,9,10,11-Tetrahydro[1,2]oxazepino[2',3':1,2]imidazo[4,5-c]quinolin-6-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 8,9,10,11-tetrahydro[1,2]oxazepino[2′,3′:1,2]imidazo[4,5-c]quinoline 5-oxide (0.1384 g, 0.5421 mmol) in 6 mL of dichloromethane was treated with 3 mL of concentrated aqueous NH4OH solution. The mixture was stirred rapidly and then p-toluenesulfonyl chloride (0.12 g, 0.65 mmol) was carefully added. Rapid stirring was continued for 40 minutes. The reaction mixture was then diluted with more dichloromethane, washed successively with dilute aqueous K2CO3, H2O and brine, dried over Na2SO4, and concentrated under reduced pressure. The solid was triturated with ether and filtered. Crystallization from acetonitrile gave 0.0369 g of 8,9,10,11-tetrahydro[1,2]oxazepino[2′,3′:1,2]imidazo[4,5-c]quinolin-6-amine as a white powder, dec. 247-255° C. MS (APCI) m/z 255 (M+H)+; Anal. calcd for C14H14N4O: C, 66.13; H, 5.55; N, 22.03. Found: C, 65.82; H, 5.27; N, 22.11.

Workup

  1. stirringRapid stirring
  2. washwashed successively with dilute aqueous K2CO3, H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe solid was triturated with ether
  6. filtrationfiltered
  7. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-4975309e48134f82959a79da958a6353
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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