(2-Chloro-4-nitrophenyl)(6,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepin-5-yl)methanone → HCID 19438743, compound

HRID 1733960Notes

Reaction equation

HRID 1733960 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[CH:17][C:3]=1[C:4]([N:6]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2[N:13]=[CH:14][CH:15]=[CH:16][C:7]1=2)=[O:5].O.O.[Cl-]>CO>[NH2:21][C:19]1[CH:18]=[CH:17][C:3]([C:4]([N:6]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]3[N:13]=[CH:14][CH:15]=[CH:16][C:7]2=3)=[O:5])=[C:2]([Cl:1])[CH:20]=1

Participants

4

Reactant 2

HCID 19699064(2-Chloro-4-nitrophenyl)(6,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepin-5-yl)methanoneHCID 21226388Chloride dihydrate

Product 1

HCID 19438743HCID 19438743, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3.31 g of 6,7,8,9-tetrahydro-5-(2-chloro-4-nitrobenzoyl)-5H-pyrido[3,2-b]azepine and 6.78 g of stannus chloride dihydrate (SnCl2.2H2O) in 200 ml of methanol is refluxed for 2 hours under argon. The solvent is removed under vacuum and 5 ml of saturated NaHCO3 solution and solid NaHCO3 added to bring the pH to 7. The mixture is extracted with ethyl acetate, the extract filtered through diatomaceous earth and the filtrate washed with saturated NaHCO3, H2O, brine and dried (Na2SO4). The filtrate is passed through a thin pad of hydrous magnesium silicate and the filtrate concentrated to dryness to give 2.58 g of an amorphous solid. Anal. Calc'd for C16H16ClN3O; C,59.9; H,5.7; N,13.1; C1, 11.1 Found: C,60.5; H,5.0; N,12.9; Cl,11.6.

Workup

  1. temperatureis refluxed for 2 hours under argon
  2. customThe solvent is removed under vacuum and 5 ml of saturated NaHCO3 solution and solid NaHCO3
  3. additionadded
  4. extractionThe mixture is extracted with ethyl acetate
  5. filtrationthe extract filtered through diatomaceous earth
  6. washthe filtrate washed with saturated NaHCO3, H2O, brine
  7. dry with materialdried (Na2SO4)
  8. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-1cf4529766dd4497becb9e5e29b67966
Source dataset
uspto-grants-1996_07
Patent number
US05532235

Reaction notes

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