Triethylamine → 1-(Bromoacetyl)-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroquinoline

HRID 1014365Notes

Reaction equation

HRID 1014365 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[NH:9][CH2:8][CH2:7][CH2:6]2.C(N(CC)CC)C.[Br:23][CH2:24][C:25](Cl)=[O:26]>ClCCl.CN(C)C1C=CN=CC=1.[Cl-].[NH4+]>[Br:23][CH2:24][C:25]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:12]([N+:13]([O-:15])=[O:14])[CH:11]=2)[CH2:6][CH2:7][CH2:8]1)=[O:26]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 89602Bromoacetyl chlorideHCID 59441908HCID 59441908, compound

Product 1

HCID 594419531-(Bromoacetyl)-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A mixture of 6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroquinoline (0.19 g, 0.91 mmol) and triethylamine (0.5 mL, 3.7 mmol, Aldrich) in dichloromethane was treated with dropwise addition of bromoacetyl chloride (0.33 mL, 4.0 mmol, Fluka). A catalytic amount of 4-dimethylaminopyridine was added and the reaction stirred overnight. The mixture was diluted with saturated aqueous ammonium chloride and extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered, and concentrated to give 1-(bromoacetyl)-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroquinoline which was taken directly to the next step without determination of yield. RF=0.3 (50% EtOAc/hexanes).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9784f06775254b43b962ff28b47ed25e
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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