Potassium Carbonate → Ethyl 6-iodo-1-(2-morpholinoethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2243053Notes

Reaction equation

HRID 2243053 reaction equation
F[C:2]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:3]=1[C:4]([C:6](=[CH:12][NH:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[I:26][C:23]1[CH:22]=[C:3]2[C:2](=[CH:25][CH:24]=1)[N:13]([CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[CH:12]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:4]2=[O:5]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178472024HCID 178472024, compound2×

Product 1

HCID 59208337Ethyl 6-iodo-1-(2-morpholinoethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 2-(2-fluoro-5-iodobenzoyl)-3-(2-morpholinoethylamino)acrylate (Intermediate 23, 358 mg, 0.75 mmol) and potassium carbonate (208 mg, 1.50 mmol) in DMF (7 mL) was heated to 100° C. for 4 h. The reaction mixture was cooled to room temperature, filtered, and concentrated under reduced pressure. The solid that formed was placed under high vacuum overnight (328 mg) to yield the desired product. MS (ESP): 457 (M+H+) for C18H21IN2O4; NMR: 1.28 (t, J=7 Hz, 3H), 2.43 (m, 4H), 2.61 (m, 2H), 3.50 (m, 4H), 4.22 (q, J=7 Hz, 2H), 4.46 (m, 2H), 7.67 (d, J=9 Hz, 1H), 8.05 (m, 1H), 8.50 (s, 1H), 8.63 (s, 1H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe solid that formed
  4. customwas placed under high vacuum overnight (328 mg)

Sources & evidence

ORD record
ord-91e0d13955024ae5b3eab593d6b80b20
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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