HCID 67406668, compound → HCID 54747342, compound

HRID 1801982Notes

Reaction equation

HRID 1801982 reaction equation
OC1C2C(=CC(C3C=CC(C(OC(C)(C)C)=O)=CC=3)=CC=2)N(C)C(=O)C=1C(=O)CCC=O.[O:33]1CCC[O:35][CH:34]1[CH2:39][CH2:40][C:41]([C:43]1[C:44](=[O:68])[N:45]([CH3:67])[C:46]2[C:51]([C:52]=1[OH:53])=[CH:50][CH:49]=[C:48]([C:54]1[CH:66]=[CH:65][C:57]([C:58]([O:60]C(C)(C)C)=[O:59])=[CH:56][CH:55]=1)[CH:47]=2)=[O:42]>CC(O)=O>[C:34]([CH2:39][CH2:40][C:41]([C:43]1[C:44](=[O:68])[N:45]([CH3:67])[C:46]2[C:51]([C:52]=1[OH:53])=[CH:50][CH:49]=[C:48]([C:54]1[CH:55]=[CH:56][C:57]([C:58]([OH:60])=[O:59])=[CH:65][CH:66]=1)[CH:47]=2)=[O:42])([OH:35])=[O:33]

Participants

4

Reactant 2

HCID 67406668HCID 67406668, compoundHCID 86631268HCID 86631268, compound

Product 1

HCID 54747342HCID 54747342, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

tert-Butyl 4-(4-hydroxy-1-methyl-2-oxo-3-(4-oxobutanoyl)-1,2-dihydroquinolin-7-yl)benzoate. AcOH (80%, 15 mL) was added to tert-butyl 4-(3-(3-(1,3-dioxan-2-yl)propanoyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-7-yl)benzoate (150 mg, 304 mmol), and the resulting mixture was heated at 90° C. for 1 hour. The reaction mixture was quenched with water and cooled to room temperature. A solid precipitated from solution and was filtered and stuck to the frit. The frit was washed with EtOAc (5×) to give the title compound as a beige solid.

Workup

  1. customThe reaction mixture was quenched with water
  2. temperaturecooled to room temperature
  3. customA solid precipitated from solution
  4. filtrationwas filtered
  5. washThe frit was washed with EtOAc (5×)

Sources & evidence

ORD record
ord-7fcdbf5dcb5f42a48a1ad4971d8ac8a5
Source dataset
uspto-grants-2013_01
Patent number
US08349868B2

Reaction notes

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