Formic Acid → HCID 66768992, compound

HRID 606471Notes

Reaction equation

HRID 606471 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([O:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=[CH:7][CH:8]=1)#[N:2].C(O)=O.[ClH:21].C(OCC)(=O)C>[C].[Pd].CO>[ClH:21].[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([O:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 21866389Hydrogen chloride-ethyl acetateHCID 57708764HCID 57708764, compound

Product 1

HCID 66768992HCID 66768992, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of ethyl 4-[(3-cyanophenyl)oxy]butanoate obtained in Reference Example 41 (8.50 g, 36.4 mmol), 10% palladium carbon (containing 50% water)(12.8 g), formic acid (98 mL) and methanol (80 mL) was stirred at room temperature for 5 hr under hydrogen atmosphere (1 atm). The precipitate was filtered off, and the filtrate was concentrated under reduced pressure. 4N Hydrogen chloride/ethyl acetate solution (15.0 mL, 60.0 mmol) was added to the obtained residue, and the mixture was stirred, and concentrated under reduced pressure. The residue was crystallized from toluene, and the crude crystals were recrystallized from diethyl ether to give the title compound as a white powder (7.79 g, 78%).

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. stirringthe mixture was stirred
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from toluene
  6. customthe crude crystals were recrystallized from diethyl ether

Sources & evidence

ORD record
ord-115d24289ba749348642416f535e2444
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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