Acetic Acid → 2-Hydroxyquinoline

HRID 1696422Notes

Reaction equation

HRID 1696422 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([N+]([O-])=O)[CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-])=O.C1(P(=[CH:34][C:35](OCC)=[O:36])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)(=O)C.C(O)C>C([O-])(=O)C=C>[NH:1]1[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:34][C:35]1=[O:36]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 682502,4-DinitrobenzaldehydeHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

Product 1

HCID 60382-Hydroxyquinoline

Reagents, catalysts & solvents 1

HCID 25188AcrylateSolvent

Procedure

Synthesis of intermediates containing A2-77 (V═O) is shown in Scheme 54. Utilizing the procedure published by Doherty et. al (see WO 03/0999284), Wittig homologation of commercially available 2,4-dinitrobenzaldehyde (251) with ethyl (triphenylphosphoranylidene)-acetate results in propenoate 252. Catalytic hydrogenation in the presence of glacial acetic acid and ethanol results in the target 1H-quinolin-2-one 253 which, utilizing the same oxidation/reduction sequence as shown in Scheme 53 results in hydrazine 254 (R15, V═O) and iodide (255). At the conclusion of the synthesis that utilizes 254 or 255, reduction of the amide with LAH under standard conditions provides an optional synthesis of intermediates containing A2-77 (V═H2).

Workup

  1. customSynthesis of intermediates
  2. additioncontaining A2-77 (V═O)

Sources & evidence

ORD record
ord-a8388252be024e8dbc56b7879db9a202
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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