Formic Acid → HCID 68679922, compound

HRID 2240075Notes

Reaction equation

HRID 2240075 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:6]=1[CH2:14][S:15]([C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)(=[O:17])=[O:16].C(O)=O>C1COCC1.CO.[Pd]>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[C:6]([CH2:14][S:15]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[C:7]([NH2:11])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 2

HCID 284Formic AcidHCID 68680105HCID 68680105, compound

Product 1

HCID 68679922HCID 68679922, compoundYield 93.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-[2-(2-Chloro-ethoxy)-6-nitro-phenylmethanesulfonyl]-naphthalene (0.9 g, 2.24 mmoles) and 10% Pd/C in THF (10 mL), methanol (10 mL), and formic acid (2 mL) was hydrogenated in a Parr hydrogenation bottle (250 mL) at 40 lb/in2 for 20 hours. The mixture was filtered through Celite, and the filtrate was diluted with EtOAc, washed with water, dried over Na2SO4, and concentrated under vacuum to afford the title compound as an off-white solid (0.78 g, 2.1 mmoles).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. additionthe filtrate was diluted with EtOAc
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-14ec65c8fd814bbab7d96f847b7ede40
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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