Water → 7-Hydroxy-3-quinolinecarbaldehyde

HRID 709895Notes

Reaction equation

HRID 709895 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.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

6

Reactant 3

HCID 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 to 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 (EA), washed (brine), dried (Na2SO4), filtered and evaporated to dryness to give the crude product, which was purified by silica gel column chromatography (PE-EA, 1:1) to give desired compound as yellow solid (1.45 g, yield 60%). ESI-MS: 216 (M+H)+. 1H NMR (300 MHz, CDCl3) δ: 7.26-7.32 (m, 2H), 8.04-8.07 (d, 1H), 8.78 (d, 1H), 9.13 (s, 1H), 10.13 (s, 1H).

Workup

  1. extractionextracted (EA)
  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 (PE-EA, 1:1)

Sources & evidence

ORD record
ord-2ad6c5a64ceb4b689b851e7187d0a817
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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