Methanol → HCID 66681926, compound

HRID 1430376Notes

Reaction equation

HRID 1430376 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[C:6](/[CH:20]=[CH:21]/[C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[CH:7]=[CH:8][C:9]=2[C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[NH:4][N:3]=1.CO.C1COCC1.[NH4+].[Cl-]>C(O)C.[Fe]>[NH2:1][C:2]1[C:10]2[C:5](=[C:6](/[CH:20]=[CH:21]/[C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[CH:7]=[CH:8][C:9]=2[C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)[NH:4][N:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 66680993HCID 66680993, compound

Product 1

HCID 66681926HCID 66681926, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A solution of Example 84C (113 mg, 0.32 mmol) in a mixture of ethanol (1 mL), methanol (1 mL), and THF (1 mL) was treated with iron powder (144 mg) and NH4Cl (17 mg), heated to 85° C. for 4 hours, cooled to room temperature, and filtered. The filtrate was partitioned between water and ethyl acetate and the organic phase was dried (MgSO4), filtered, and concentrated. The residue was purified by flash column chromatography on silica gel with 5% methanol/dichloromethane to provide 75 mg of the desired product. MS (ESI(+)) m/e 322 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customThe filtrate was partitioned between water and ethyl acetate
  4. dry with materialthe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography on silica gel with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-26c644657a3a46ccbe1f4034810fa618
Source dataset
uspto-grants-2015_01
Patent number
US08940778B2

Reaction notes

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