3,5-Dichlorosalicylaldehyde → HCID 86649074, compound

HRID 2070130Notes

Reaction equation

HRID 2070130 reaction equation
[NH2:1][CH:2]1[CH2:11][C:10]2[C:5](=[C:6]([N:12]3[CH2:16][CH2:15][CH2:14][C:13]3=[O:17])[CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:18][C:19]2[CH:23]=[CH:22][S:21][CH:20]=2)[C:3]1=[O:24].ClC1C=C(Cl)C=C(C=O)C=1O.[C:36]([OH:45])(=[O:44])[C@H:37]([C@@H:39]([C:41]([OH:43])=[O:42])[OH:40])[OH:38]>CO>[C:41]([C@H:39]([C@@H:37]([C:36]([OH:45])=[O:44])[OH:38])[OH:40])([OH:43])=[O:42].[NH2:1][CH:2]1[CH2:11][C:10]2[C:5](=[C:6]([N:12]3[CH2:16][CH2:15][CH2:14][C:13]3=[O:17])[CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:18][C:19]2[CH:23]=[CH:22][S:21][CH:20]=2)[C:3]1=[O:24]

Participants

5

Reactant 3

HCID 666603,5-DichlorosalicylaldehydeHCID 439655D-Tartaric acidHCID 596203303-amino-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 86649074HCID 86649074, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

3-Amino-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-3,4-dihydroquinolin-2(1H)-one (418 g) was dissolved in methanol (3.1 L), and 3,5-dichlorosalicylaldehyde (17.2 g) and D-(−)-tartaric acid (136 g) were added thereto, followed by stirring at 60° C. for 11 hours. The reaction mixture was left to stand to cool, and the formed precipitates were recovered through filtration. The thus-obtained solid was washed with methanol and dried, whereby the title compound (271 g) (97.8% ee) was yielded as a powdery compound.

Workup

  1. waitThe reaction mixture was left
  2. temperatureto cool
  3. customthe formed precipitates
  4. filtrationwere recovered through filtration
  5. washThe thus-obtained solid was washed with methanol
  6. customdried

Sources & evidence

ORD record
ord-2abdcc519282406a9fb54878b6171414
Source dataset
uspto-grants-2012_10
Patent number
US08299255B2

Reaction notes

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