Hydrochloric Acid → 5,8-Bis(2,2,2-trifluoroethoxy)quinoline-6,7-dicarboxylic acid

HRID 907469Notes

Reaction equation

HRID 907469 reaction equation
[F:1][C:2]([F:32])([F:31])[CH2:3][O:4][C:5]1[C:14]([C:15]([O:17]CC)=[O:16])=[C:13]([C:20]([O:22]CC)=[O:21])[C:12]([O:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2.[OH-].[Na+].[NH4+].[Cl-].Cl>CO.C1COCC1>[F:32][C:2]([F:1])([F:31])[CH2:3][O:4][C:5]1[C:14]([C:15]([OH:17])=[O:16])=[C:13]([C:20]([OH:22])=[O:21])[C:12]([O:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 44245003Diethyl 5,8-bis(2,2,2-trifluoroethoxy)quinoline-6,7-dicarboxylate

Product 1

HCID 442453435,8-Bis(2,2,2-trifluoroethoxy)quinoline-6,7-dicarboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution containing diethyl 5,8-bis(2,2,2-trifluoroethoxy)quinoline-6,7-dicarboxylate 3 (84.7 g, 180 mmol), 5 N NaOH (180 ml), THF (360 ml) and MeOH (180 ml) was heated to 60 C for 1.5 h. This mixture was then added to half-saturated NH4Cl and acidified with 2 N HCl to pH 0-1. The product was extracted into i-PrOAc:THF 1:1, dried over Na2SO4 and concentrated. It was triturated with ether:hexane 1:4 to yield the diacid 4 as an off-white solid (approx 100% yield).

Workup

  1. temperaturewas heated to 60 C for 1.5 h
  2. extractionThe product was extracted into i-PrOAc:THF 1:1
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customIt was triturated with ether:hexane 1:4

Sources & evidence

ORD record
ord-ff6902a1964b4d4cb591fd082d975a66
Source dataset
uspto-grants-2011_09
Patent number
US08013159B2

Reaction notes

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