Tetrahydrofuran → HCID 14171581, compound

HRID 1639260Notes

Reaction equation

HRID 1639260 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:15])[C:7]3[N:8]([CH:12]=[CH:13][CH:14]=3)[NH:9][C:10]=2[CH:11]=1.O1CCC[CH2:17]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[N:9][N:8]1[CH:12]=[CH:13][CH:14]=[C:7]1[C:6]=2[O:15][CH3:17]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 14171570HCID 14171570, compound

Product 1

HCID 14171581HCID 14171581, compound

Procedure

Diazomethane was prepared by adding Diazald® (21.4 g) in 200 ml of ether to potassium hydroxide (5.0 g) in 20 ml of 50% ethanol/water solution and then distilling. This procedure was followed three times to give a solution of diazomethane (16.25 g) in ether which was then added to a stirred slurry of 7-chloropyrrolo[1,2-b]cinnolin-10(5H)-one (37.0 g) in 250 ml of tetrahydrofuran. The mixture was allowed to stand at room temperature for 48 hours and then the volatiles were removed. The residue was taken up in dichloromethane and washed several times with water. The organic layer was dried (MgSO4), filtered and concentrated to a dark orange powder. The powder was purified by flash chromatography (silica, dichloromethane) to give 18.35 g of an orange powder. A five gram portion of this powder was recrystallized from ether to give 4.3 g of an orange fibrous material, mp 128°-129°.

Workup

  1. customthe volatiles were removed
  2. washwashed several times with water
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to a dark orange powder
  6. customThe powder was purified by flash chromatography (silica, dichloromethane)

Sources & evidence

ORD record
ord-f844b2bb2ba641cebddabefd38841922
Source dataset
uspto-grants-1989_11
Patent number
US04883794

Reaction notes

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