Methanol → HCID 67040286, compound

HRID 605264Notes

Reaction equation

HRID 605264 reaction equation
[CH2:1]([O:8][C:9]1[CH:34]=[CH:33][C:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)=[CH:16][C:15]=2[N+:30]([O-])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].CO.C1COCC1>[Fe].O>[NH2:30][C:15]1[CH:16]=[C:17]([NH:20][C:21](=[O:29])[C:22]2[CH:23]=[CH:24][C:25]([Br:28])=[CH:26][CH:27]=2)[CH:18]=[CH:19][C:14]=1[O:13][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 67040236HCID 67040236, compound

Product 1

HCID 67040286HCID 67040286, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

The product from Example 247b (1.18 g, 2.27 mmol), iron powder (0.51 g, 9.1 mmol) and ammonium chloride (0.14 g, 2.5 mmol) in a methanol (10 ml), THF (10 ml) and water (5 mL) solution was heated at reflux for 1.5 hr. The resultant mixture was filtered, rinsed with hot methanol (50 ml) and concentrated under vacuum to an oily residue. The residue was diluted with ethyl acetate (100 ml) and washed with water and 10% sodium chloride, then dried over anhydrous sodium sulfate. The drying agent was filtered and the organic solvent was removed under vacuum providing the title compound (0.81 g, 73%).

Workup

  1. temperatureat reflux for 1.5 hr
  2. filtrationThe resultant mixture was filtered
  3. washrinsed with hot methanol (50 ml)
  4. concentrationconcentrated under vacuum to an oily residue
  5. additionThe residue was diluted with ethyl acetate (100 ml)
  6. washwashed with water and 10% sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe drying agent was filtered
  9. customthe organic solvent was removed under vacuum

Sources & evidence

ORD record
ord-dce702690c1f4d88941e48ebb03a599d
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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