HCID 22452635, compound → HCID 22452630, compound

HRID 2185901Notes

Reaction equation

HRID 2185901 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:15]([OH:17])=[O:16]>CC(O)=O.[Pd]>[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[C:4]=1[C:15]([OH:17])=[O:16]

Participants

4

Reactant 1

HCID 22452635HCID 22452635, compound

Product 1

HCID 22452630HCID 22452630, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2,3-dimethoxy-1-naphthalenecarboxylic acid (2.21 g, 9.52 mmol) and 10% Pd/C (0.53 g) in HOAc (50 mL) was hydrogenated on a Parr apparatus at 60° C. and 50 psi for 11 h. After filtration through diatomaceous earth, the solvent was removed under reduced pressure, and water was added. The precipitate was filtered and washed with water to give the product as a white solid (1.62 g, 72%). 1H NMR (DMSO-d6) δ 12.99 (s, 1H), 6.77 (s,1H), 3.77 (s, 3H), 3.68 (s, 3H), 2.67 (s, 2H), 2.50 (s, 2H), 1.68 (m, 4H); MS m/z 235 (m−H).

Workup

  1. customwas hydrogenated on a Parr apparatus at 60° C.
  2. filtrationAfter filtration through diatomaceous earth
  3. customthe solvent was removed under reduced pressure, and water
  4. additionwas added
  5. filtrationThe precipitate was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-dca4e27cc94445ce82956a360d78d409
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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