Methanol → HCID 86644275, compound

HRID 2265090Notes

Reaction equation

HRID 2265090 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1/[C:11](/[CH3:20])=[CH:12]/[C:13]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14].[Cl-].[NH4+].O1CCCC1.CO>[Fe].O>[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1/[C:11](/[CH3:20])=[CH:12]/[C:13]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14]

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 86644274HCID 86644274, compound

Product 1

HCID 86644275HCID 86644275, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Compound 5a (1.05 g), iron powder (1.11 g), and ammonium chloride (0.32 g) were added to a mixed solution of tetrahydrofuran (4 ml), methanol (4 ml), and water (4 ml). The mixture was stirred at 60° C. for 2 hours. The same amount of iron powder and ammonium chlorides were further added thereto, and the obtained mixture was stirred at 70° C. for 1 hour. After the reaction mixture was allowed to cool, and filtered, insoluble substances were filtered through Celite. The filtrate was condensed under reduced pressure to give Compound 5b (939 mg).

Workup

  1. stirringthe obtained mixture was stirred at 70° C. for 1 hour
  2. temperatureto cool
  3. filtrationfiltered
  4. filtrationinsoluble substances were filtered through Celite
  5. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-4ab5f621f4034e52aeb3cdfdbe355171
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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