HCID 66989070, compound → HCID 45091006, compound

HRID 2407765Notes

Reaction equation

HRID 2407765 reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[C:8]([C:10]#[N:11])[C:7]([N+:12]([O-])=O)=[CH:6][CH:5]=1)[CH3:2]>Cl.CO.[Fe]>[NH2:12][C:7]1[C:8]([C:10]#[N:11])=[N:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=1

Participants

5

Reactant 1

HCID 66989070HCID 66989070, compound

Product 1

HCID 45091006HCID 45091006, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a suspension of the compound prepared in Example 280 (0.672 g) in hydrochloric acid (2.3 mL) and methanol (7 mL) was added portionwise iron (0.680 g) slowly. After addition was complete, the mixture was stirred at room temperature for 1 hour. The mixture was evaporated in vacuo, diluted with dichloromethane, filtered, and purified by column chromatography on silica gel (5-70% ethyl acetate in hexane) to obtain the title compound (0.460 g) having the following physical data.

Workup

  1. additionAfter addition
  2. customThe mixture was evaporated in vacuo
  3. additiondiluted with dichloromethane
  4. filtrationfiltered
  5. custompurified by column chromatography on silica gel (5-70% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-27cda08e4518474b80fd5d40880d2d60
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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