Water → 8,9,10,11-Tetrahydro[1,2]oxazepino[2',3':1,2]imidazo[4,5-c]quinoline

HRID 415511Notes

Reaction equation

HRID 415511 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]([OH:19])[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1.[H-].[Na+].O>CN(C=O)C>[CH:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[C:8]1[N:7]3[O:19][CH2:2][CH2:3][CH2:4][CH2:5][C:6]3=[N:18][C:9]=1[CH:10]=[N:11]2

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 666210712-(4-chlorobutyl)-1H-imidazo[4,5-c]quinolin-1-ol

Product 1

HCID 666200338,9,10,11-Tetrahydro[1,2]oxazepino[2',3':1,2]imidazo[4,5-c]quinolineYield 106.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 2-(4-chlorobutyl)-1H-imidazo[4,5-c]quinolin-1-ol (0.167 g, 0.606 mmol) in 6 mL of anhydrous DMF was treated with 60% NaH in mineral oil (0.032 g, 0.787 mmol). After 45 minutes the mixture was poured into 20 mL of water and washed with ethyl acetate. The organic portions were combined, washed successively with dilute aqueous K2CO3, H2O, and brine, dried over Na2SO4, and concentrated under reduced pressure to give 0.154 g of 8,9,10,11-tetrahydro[1,2]oxazepino[2′,3′:1,2]imidazo[4,5-c]quinoline as a tan solid.

Workup

  1. washwashed with ethyl acetate
  2. washwashed successively with dilute aqueous K2CO3, H2O, and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4ae57e479f3d4bcab271d28c0c8620e5
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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