Pyridine → HCID 67264032, compound

HRID 1687927Notes

Reaction equation

HRID 1687927 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:8][CH2:7][CH2:6][NH:5][C:4]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:3]1=2.N1C=CC=CC=1.[Cl:23][CH2:24][C:25](Cl)=[O:26]>CN(C)C1C=CN=CC=1.ClCCCl>[Cl:23][CH2:24][C:25]([N:5]1[CH2:6][CH2:7][CH2:8][C:2]([CH3:16])([CH3:1])[C:3]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:4]1=2)=[O:26]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 574702565,5-dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine

Product 1

HCID 67264032HCID 67264032, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

5,5-Dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine (0.837 g, 3.80 mmol), pyridine (0.408 mL, 5.04 mmol) and 4-dimethylaminopyridine (14.4 mg, 0.118 mmol) were dissolved in anhydrous 1,2-Dichloroethane (9.0 mL) before adding chloroacetyl chloride (0.403 mL, 5.07 mmol). The reaction was stirred at room temperature for 3 hours, washed sequentially with 1 N HCl, water, saturated sodium bicarbonate solution and brine. The organic phase was dried with magnesium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with ether (6 mL×2) to yield a crude brown solid, 2-Chloro-1-(5,5-dimethyl-8-nitro-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl)-ethanone. LCMS: m/z=297.42 (M+H+).

Workup

  1. washwashed sequentially with 1 N HCl, water, saturated sodium bicarbonate solution and brine
  2. dry with materialThe organic phase was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was triturated with ether (6 mL×2)

Sources & evidence

ORD record
ord-f755c12d732a4f6598f7943f381478e0
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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