Triethylamine → HCID 86626639, compound

HRID 2404978Notes

Reaction equation

HRID 2404978 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20].[CH2:22](N)[C:23]#[CH:24]>O1CCCC1>[Cl:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:24][C:23]#[CH:22])[CH2:11][C:10]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 239041PropargylamineHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 86626639HCID 86626639, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (8.0 mL, 1.2 eq.) was added to a mixture of 4-chloro-3-nitroquinoline (10.0 g, 47.9 mmol, 1.0 eq.) in tetrahydrofuran (THF, 200 mL). Propargylamine (3.4 mL, 1.1 eq.) was added and the reaction mixture was stirred vigorously for 1.5 hours. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between chloroform (700 mL) and water (200 mL). The organic layer was washed with water (1×200 mL). The combined aqueous layers were back extracted with chloroform (2×150 mL). The combined organics were dried over magnesium sulfate and concentrated under reduced pressure to provide 10.59 g of 4-chloro-3-nitro-N-(2-propynyl)quinoline as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between chloroform (700 mL) and water (200 mL)
  3. washThe organic layer was washed with water (1×200 mL)
  4. extractionThe combined aqueous layers were back extracted with chloroform (2×150 mL)
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7c27101a5d04805b00688ee7f235aa3
Source dataset
uspto-grants-2014_08
Patent number
US08802853B2

Reaction notes

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