Quinaldic Acid → HCID 19692229, compound

HRID 862668Notes

Reaction equation

HRID 862668 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.S(C1C=CC(C)=CC=1)(O)(=O)=[O:15].[CH2:25]([O:32][C:33](=[O:36])[CH2:34][NH2:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH:37]1[CH:38]=[CH:39][C:40]2N(O)N=N[C:41]=2[CH:42]=1.[CH3:47][CH2:48][CH2:49]CCCC.[C:54](OCC)(=[O:56])C>C(Cl)Cl>[CH2:25]([O:32][C:33](=[O:36])[CH2:34][NH:35][C:11]([C:2]1[C:3]([O:56][CH2:54][C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:42]=2)=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[C:7]([O:15][CH:48]([CH3:49])[CH3:47])[CH:6]=2)[N:1]=1)=[O:13])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 7124Quinaldic AcidHCID 757711-HydroxybenzotriazoleHCID 6451311O-benzylglycine toluene-p-sulphonateHCID 21899848Ethylacetate heptane

Product 1

HCID 19692229HCID 19692229, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.7 g (8 mmol) of the above quinolinecarboxylic acid were reacted with 2.7 g (8 mmol) of glycine benzyl ester tosylate, 4.4 ml (32 mmol) of NEM, 1.35 g (10 mmol) of HOBT and 3.6 g (8.8 mmol) of CMC in 300 ml of anhydrous methylene chloride at 20° C. for 24 hours, analogously to Example 25g). After working up and chromatography over silica gel with n-heptane/ethyl acetate (3:2), 3.5 g of oily product were obtained.

Sources & evidence

ORD record
ord-b391819defb046e0a2069e6998a6dc58
Source dataset
uspto-grants-1998_02
Patent number
US05719164

Reaction notes

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