Methanol → HCID 18691332, compound

HRID 1871353Notes

Reaction equation

HRID 1871353 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]([CH2:28][CH3:29])[C:12]1[N:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-])=O)[CH:15]=[C:14]([CH3:27])[N:13]=1.CO>[Fe].C(O)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]([CH2:28][CH3:29])[C:12]1[N:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH2:24])[CH:15]=[C:14]([CH3:27])[N:13]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 10095518HCID 10095518, compound

Product 1

HCID 18691332HCID 18691332, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 176Acetic AcidSolvent

Procedure

The product of Example 11 (778 mg), methanol (40.5 mL), acetic acid (13.5 mL) and iron powder (382 mg) were heated at reflux and stirred mechanically for 6 h. More iron powder (1.15 g) was added and the reaction was heated at reflux 2 more hours, after which it was cooled, filtered through celite, and concentrated to a thick black oil. Added ethyl acetate (200 mL) and water (100 mL), stirred, and filtered through celite. The layers were separated and the ethyl acetate dried over MgSO4 and concentrated to a thick yellow oil (754 mg). The oil was chromatographed on silica gel using ethyl acetate/hexane (1:9) as eluent. The title compound was obtained as an off-white solid (526 mg). CI-HRMS calc'd. for C22H26N4Br (M+H)+ : 425.134083. Found: 425.131850.

Workup

  1. temperatureat reflux
  2. temperaturethe reaction was heated
  3. temperatureat reflux 2 more hours
  4. temperatureafter which it was cooled
  5. filtrationfiltered through celite
  6. concentrationconcentrated to a thick black oil
  7. stirringAdded ethyl acetate (200 mL) and water (100 mL), stirred
  8. filtrationfiltered through celite
  9. customThe layers were separated
  10. dry with materialthe ethyl acetate dried over MgSO4
  11. concentrationconcentrated to a thick yellow oil (754 mg)
  12. customThe oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-a026fee984664d9c8cd7049125da4495
Source dataset
uspto-grants-2000_08
Patent number
US06103737

Reaction notes

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