Acetic Acid → 5-Chloro-1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

HRID 2425760Notes

Reaction equation

HRID 2425760 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][CH:11]([CH3:13])[CH3:12])[C:3]=1[CH:4]=O.C(N)CN.C(O)(=O)C.CC1(C)O[C:28](=[O:29])[CH2:27][C:25](=[O:26])[O:24]1>CO>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:3]=1[CH:4]=[C:27]([C:25]([OH:26])=[O:24])[C:28](=[O:29])[N:10]2[CH:11]([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3301EthylenediamineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 598224892-Chloro-6-(isopropylamino)benzaldehyde

Product 1

HCID 598224655-Chloro-1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acidYield 14%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-chloro-6-(isopropylamino)benzaldehyde (1.1 g, 5.57 mmol, step 3) in methanol (10 mL) was added ethylenediamine (0.186 mL, 2.78 mmol) and acetic acid (0.319 mL, 5.57 mmol). Meldrum's acid (1.6 g, 11.1 mmol) was added to the mixture at 0° C. Then, the mixture was stirred at room temperature for 16 h. The formed precipitate was filtrated and washed with methanol. The filtrate was evaporated and crystallized from methanol to give 200 mg (14%) of the title compound as a white solid.

Workup

  1. filtrationThe formed precipitate was filtrated
  2. washwashed with methanol
  3. customThe filtrate was evaporated
  4. customcrystallized from methanol

Sources & evidence

ORD record
ord-63934a61a9ee4c3ebd4f4e730ba17744
Source dataset
uspto-grants-2011_06
Patent number
US07964727B2

Reaction notes

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