Ethanol → HCID 178469634, compound

HRID 1168523Notes

Reaction equation

HRID 1168523 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH3:29])[CH:9]=[C:10]2[C:15]=1[N:14](C(OCC(C)C)=O)[CH:13]=[C:12]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:11]2=[O:28])(=O)C.BrN1C(=O)CCC1=O.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.C(O)C>ClCCl>[CH:5]([C:6]1[CH:7]=[C:8]([CH2:29][N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)[CH:9]=[C:10]2[C:15]=1[N:14]=[CH:13][C:12]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:11]2[OH:28])=[O:4]

Participants

6

Reactant 4

HCID 702EthanolHCID 8083MorpholineHCID 67184N-bromobutanimideHCID 12083049HCID 12083049, compound

Product 1

HCID 178469634HCID 178469634, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 3-ethyl 1-isobutyl 8-((acetyloxy)methyl)-6-methyl-4-oxo-1,3-(4H)-quinolinedicarboxylate (Preparation 26, 3.0 g) and N-bromosuccinimide (3.0 g) in dichloromethane (300 mL) is irradiated with a 650 watt sun lamp for 20 min. Morpholine (15 mL) is added to the solution. After 10 min, ethanol (20 mL) is added, and the solvents are removed at 50° C./20 mm. The reaction is repeated on the same scale. The reaction mixtures are combined and partitioned between chloroform (250 mL) and water (150 mL). The chloroform layer is washed twice with water, and the chloroform is evaporated. The residual oil is chromatographed on silica gel (1% methanol/chloroform) to give 2.15 g of the title compound. Physical characteristics: M.p. 202-204° C.; 1H NMR (CDCl3) δ1.43, 2.50, 3.69, 3.74, 4.42, 8.19, 8.59, 8.67, 10.18, 11.8. Anal. Found: C, 62.42; H, 5.92; N, 8.03.

Workup

  1. customthe solvents are removed at 50° C./20 mm
  2. customThe reaction mixtures
  3. custompartitioned between chloroform (250 mL) and water (150 mL)
  4. washThe chloroform layer is washed twice with water
  5. customthe chloroform is evaporated
  6. customThe residual oil is chromatographed on silica gel (1% methanol/chloroform)

Sources & evidence

ORD record
ord-5601806979af4fde880c2ac5900e70a9
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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