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

HRID 1014362Notes

Reaction equation

HRID 1014362 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.[C:23](Cl)(=[O:26])[CH:24]=[CH2:25]>ClCCl.CN(C)C1C=CN=CC=1.[Cl-].[NH4+]>[C:23]([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])[CH:24]=[CH2:25]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 594419086-(Methyloxy)-7-nitro-1,2,3,4-tetrahydroquinoline

Product 1

HCID 594418921-Acryloyl-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, 3.6 mmol, Aldrich) in dichloromethane was treated with dropwise addition of acryloyl chloride (0.3 mL, 3.7 mmol, Pfaltz and Bauer). 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 ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated to give 1-acryloyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroquinoline which was taken directly to the next step without determination of yield. ESIMS (M+H)+=263.

Workup

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

Sources & evidence

ORD record
ord-28fb178c44294323a97adedd40832a06
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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