HCID 21875489, compound → HCID 21875293, compound

HRID 723678Notes

Reaction equation

HRID 723678 reaction equation
[N+:1]([C:4]1[C:13]2[N:12]=[CH:11][CH:10]=[N:9][C:8]=2[C:7]([C:14]#[N:15])=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.[Fe]>[NH2:1][C:4]1[C:13]2[N:12]=[CH:11][CH:10]=[N:9][C:8]=2[C:7]([C:14]#[N:15])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 21875489HCID 21875489, compound

Product 1

HCID 21875293HCID 21875293, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Compound 468A (0.200 g, 1.00 mmol) was suspended in acetic acid (5.0 ML) and iron powder (325 mesh, 0.112 g, 2.00 mmol) was added. The reaction was then heated at 70° C. for 20 min and then cooled to 22° C. The reaction was filtered through Celite, rinsing with ethyl acetate. The ethyl acetate rinse was collected and washed with sat. aq. K2CO3. The aqueous layer was extracted with ethyl acetate (3×20 mL) and the combined organic layers were dried over anhydrous magnesium sulfate. Concentration in vacuo gave 0.170 g (100%) of compound 468B as a yellow solid. HPLC: 88% at 1.677 min (retention time) (YMC S5 ODS column, 4.6×50 mm, eluting with 10–90% aqueous methanol over 4 min containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 171.29 [M+H]+.

Workup

  1. temperaturecooled to 22° C
  2. filtrationThe reaction was filtered through Celite
  3. washrinsing with ethyl acetate
  4. washThe ethyl acetate rinse
  5. customwas collected
  6. washwashed with sat. aq. K2CO3
  7. extractionThe aqueous layer was extracted with ethyl acetate (3×20 mL)
  8. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  9. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-39b39f7aa5e14a539df7559de27b3d23
Source dataset
uspto-grants-2006_11
Patent number
US07141578B2

Reaction notes

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