Formic Acid → 7-Hydroxy-3-quinolinecarbaldehyde

HRID 1802068Notes

Reaction equation

HRID 1802068 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([CH:16]=[O:17])[C:11](Cl)=[N:12]2)=[CH:7][CH:6]=1)(=O)C.CCN(CC)CC.C(O)=O.O>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([CH:16]=[O:17])[CH:11]=[N:12]2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 8471TriethylamineHCID 85990114HCID 85990114, compound

Product 1

HCID 1356489667-Hydroxy-3-quinolinecarbaldehydeYield 60%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-chloro-3-formylquinolin-7-yl acetate (2.9 g, 14 mmol) and Pd(PPh3)4 (1.6 g, 1.4 mmol, 0.1 eq.), Et3N (17 g, 168 mmol, 16 eq.) in DMF (100 mL) was added formic acid (3.48 g, 75.6 mmol, 5.4 eq.) dropwise over 5 min. The mixture was warmed to 110° C. over 2 h. Then, the reaction mixture was diluted (water), extracted (ethyl acetate), washed (brine), dried (Na2SO4), filtered and evaporated to dryness to give the crude product, which was purified by silica gel column chromatography (pet. ether:ethyl acetate, 1:1) to give 7-hydroxyquinoline-3-carbaldehyde as yellow solid (1.45 g, yield 60%). ESI-MS: 216 (M+H)+.

Workup

  1. extractionextracted (ethyl acetate)
  2. washwashed (brine)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto give the crude product, which
  7. customwas purified by silica gel column chromatography (pet. ether:ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-e363fe2a1d8c487788ccd18a9570c904
Source dataset
uspto-grants-2013_01
Patent number
US08349849B2

Reaction notes

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