HCID 22452679, compound → HCID 22452660, compound

HRID 2185898Notes

Reaction equation

HRID 2185898 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]([OH:17])=[O:16])[C:6]2[C:11]([C:12]=1[O:13][CH3:14])=[CH:10][CH:9]=[CH:8][CH:7]=2>CC(O)=O.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]([OH:17])=[O:16])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[C:12]=1[O:13][CH3:14]

Participants

4

Reactant 1

HCID 22452679HCID 22452679, compound

Product 1

HCID 22452660HCID 22452660, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 3,4-dimethoxy-1-naphthalenecarboxylic acid (2.34 g, 10.1 mmol) and 10% Pd/C (0.56 g) in HOAc (50 mL) was hydrogenated on Parr apparatus at 60° C. and 50 psi for 14 h. After filtration through diatomaceous earth, the solvent was removed in vacuo and water was added. The solid was collected by filtration and washed with water to yield the title compound as a yellow solid (2.21 g, 93%). 1H NMR (DMSO-d6) δ 12.69 (s, 1H), 7.30 (s, 1H), 3.79 (s, 3H), 3.73 (s, 3H), 2.91 (s, 2H), 2.65 (s, 2H), 1.64 (m, 4H); MS m/z 235 (M−H).

Workup

  1. customwas hydrogenated on Parr apparatus at 60° C.
  2. filtrationAfter filtration through diatomaceous earth
  3. customthe solvent was removed in vacuo and water
  4. additionwas added
  5. filtrationThe solid was collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-6fde6abb8af142c9a2fb9e3051b25bf6
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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