Water → HCID 54512856, compound

HRID 1582210Notes

Reaction equation

HRID 1582210 reaction equation
C([CH:3]([C:7](Cl)=[O:8])[C:4](Cl)=[O:5])C.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)([OH:24])[C:18]2[N:22]([CH3:23])[CH:21]=[N:20][CH:19]=2)=[CH:13][C:12]=1[C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=1)=O.N1[CH:46]=[CH:45]C=CC=1.[OH2:47]>C(Cl)Cl>[Cl:40][C:36]1[CH:35]=[C:34]([C:32]2[C:12]3[C:11](=[CH:16][CH:15]=[C:14]([C:17]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)([OH:24])[C:18]4[N:22]([CH3:23])[CH:21]=[N:20][CH:19]=4)[CH:13]=3)[NH:10][C:7](=[O:8])[C:3]=2[C:4]([O:5][CH2:45][CH3:46])=[O:47])[CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 109209242-Ethylpropanedioyl dichlorideHCID 22714353HCID 22714353, compound

Product 1

HCID 54512856HCID 54512856, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of ethyl malonyl chloride (6.4 ml) in DCM (50 ml) was added dropwise at room temperature to a solution of intermediate (6-d) (15 g) and pyridine (10.7 ml) in DCM (150 ml). The mixture was stirred at room temperature overnight. Water was added and the mixture was decanted. The organic layer was dried, filtered and the solvent was evaporated. The residue (21 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/2-propanol/NH4OH 92/8/0.4). The desired fractions were collected and the solvent was evaporated, yielding 10.9 g (60%) of (±)-ethyl 4-(3-chlorophenyl)-6-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-1,2-dihydro-2-oxo-3-quinolinecarboxylate (comp. 144).

Workup

  1. customthe mixture was decanted
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe residue (21 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/2-propanol/NH4OH 92/8/0.4)
  6. customThe desired fractions were collected
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8e6f795e55e34c25ab77afd752709b38
Source dataset
uspto-grants-2004_05
Patent number
US06734194B2

Reaction notes

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