Citric Acid → HCID 18333007, compound

HRID 2269740Notes

Reaction equation

HRID 2269740 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]([C:13]([OH:15])=O)[CH2:5]2.Cl.[CH3:17][NH:18][CH3:19].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(#N)C.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]([C:13]([N:18]([CH3:19])[CH3:17])=[O:15])[CH2:5]2

Participants

8

Reactant 5

HCID 311Citric AcidHCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 18333062HCID 18333062, compound

Product 1

HCID 18333007HCID 18333007, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

6-Chloro-2-oxo-1,2,3,4-tetrahydro-3-quinolinecarboxylic acid (3.00 g), dimethylamine hydrochloride (1.332 g), HOBt (2.042 g), WSC (3.093 g) and triethylamine (4.5 ml) were added to acetonitrile (150 ml). The reaction mixture was stirred at room temperature for 18 hours. 10% Aqueous citric acid solution was added to the reaction mixture. The precipitated pellets were collected by filtration and washed with water and IPE to obtain the entitled compound (1.276 g).

Workup

  1. filtrationThe precipitated pellets were collected by filtration
  2. washwashed with water and IPE

Sources & evidence

ORD record
ord-ca0e137bed6f4d13acd888bbb052cdc9
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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