Quinaldic Acid → Benzyl Alcohol

HRID 2221454Notes

Reaction equation

HRID 2221454 reaction equation
N1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=CC=1C(O)=O.C(N1C=CN=C1)([N:16]1[CH:20]=[CH:19][N:18]=[CH:17]1)=[O:15]>CCOC(C)=O>[N-:16]1[CH:20]=[CH:19][N:18]=[CH:17]1.[CH2:4]([OH:15])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 7124Quinaldic AcidHCID 682631,1'-Carbonyldiimidazole

Product 2

HCID 244Benzyl AlcoholHCID 3386966Imidazolate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The carboxylic acid functionality in the quinolinecarboxylic acid (A) is protected using standard carboxylic acid protection procedures well known in the art, e.g., by formation of the corresponding ester, to give compound (B). For example, the benzyl ester (R21 is benzyl in (B)) may be prepared by treating a solution of compound (A) in EtOAc at room temperature with 1,1′-carbonyldiimidazole to produce the activated, imidazolide derivative of (A, then adding benzyl alcohol to the reaction mixture.

Sources & evidence

ORD record
ord-8080a24a10414beab4f64618a523f097
Source dataset
uspto-grants-2008_05
Patent number
US07368573B2

Reaction notes

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