Diisopropylethylamine → N-Methoxy-2-pyridin-2-yl-3,4-dihydroquinoline-1(2H)-carboxamide

HRID 589097

Reaction equation

HRID 589097 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8]1.[CH3:17][O:18][NH:19][C:20](=O)[O:21]C1C=CC([N+]([O-])=O)=CC=1.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[CH3:17][O:18][NH:19][C:20]([N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:15][CH2:16][CH:7]1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:21]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 115647354-Nitrophenyl methoxycarbamateHCID 904098222-Pyridin-2-yl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 90408927N-Methoxy-2-pyridin-2-yl-3,4-dihydroquinoline-1(2H)-carboxamideYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-pyridin-2-yl-1,2,3,4-tetrahydroquinoline (0.723 g, 3.44 mmol) in methylene chloride (10.3 mL) was treated with 4-nitrophenyl methoxycarbamate (0.948 g, 4.47 mmol) (Org. Process Res. Dev. 2012, 16, 109-116) followed by the dropwise addition of N,N-diisopropylethylamine (1.20 mL, 6.88 mmol), and the resulting mixture was stirred at room temperature for 1.5 h. The reaction mixture was then poured over water (25 mL) and saturated sodium bicarbonate (25 mL) and extracted with dichloromethane (2×50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to give a crude oily solid. Purification by flash column chromatography (100% hexanes to 20% ethyl acetate/hexanes [the ethyl acetate contained 5% methanol]) gave the desired product (0.923 g, 95%) as a racemic mixture. LCMS calculated for C16H18N3O2 (M+H)+: m/z=284.1. found: 284.0.

Workup

  1. extractionextracted with dichloromethane (2×50 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude oily solid
  6. customPurification by flash column chromatography (100% hexanes to 20% ethyl acetate/hexanes [the ethyl acetate

Sources & evidence

ORD record
ord-ab994f55efbd452aa72be3d56fa76a88
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Linked notes

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