Ammonia → HCID 19606260, compound

HRID 1603900Notes

Reaction equation

HRID 1603900 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:14][C:13]2[CH:15]=[C:16]([C:19]([NH:21][C:22]3[C:31]4[O:30][C:29]([C:32]([O:34]CC)=O)=[CH:28][C:27](=[O:37])[C:26]=4[CH:25]=[CH:24][CH:23]=3)=[O:20])[CH:17]=[CH:18][C:12]=2[O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:38]>CO.O1CCCC1>[O:37]=[C:27]1[C:26]2[CH:25]=[CH:24][CH:23]=[C:22]([NH:21][C:19]([C:16]3[CH:17]=[CH:18][C:12]4[O:11][CH:10]([CH2:9][O:8][CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)[CH2:14][C:13]=4[CH:15]=3)=[O:20])[C:31]=2[O:30][C:29]([C:32](=[O:34])[NH2:38])=[CH:28]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 19606283HCID 19606283, compound

Product 1

HCID 19606260HCID 19606260, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a solution of ethyl 8-(2-benzyloxymethyl-2,3-dihydrobenzofuran-5-carboxamido)-4-oxo-4H-1-benzopyran-2-carboxylate (528 mg, 1.06 mmol) in methanol (25 ml) and anhydrous tetrahydrofuran (25 ml), ammonia gas was bubbled for 30 minutes. After evaporation to dryness, the resulting solid residue was dissolved in a tetrahydrofuran:methanol 1:1 mixture (15 ml) and added with concentrated HCl (0.5 ml). The mixture was refluxed under stirring for 1.5 h, then the solvents were evaporated off under reduced pressure. The resulting crude was suspended in water and the insoluble solid was recovered by filtration, washed repeatedly with water and dried under vacuum on phosphorous pentoxyde, thereby obtaining 527 mg of the title compound (quantitative yield).

Workup

  1. customAfter evaporation to dryness
  2. dissolutionthe resulting solid residue was dissolved in a tetrahydrofuran:methanol 1:1 mixture (15 ml)
  3. additionadded with concentrated HCl (0.5 ml)
  4. temperatureThe mixture was refluxed
  5. customthe solvents were evaporated off under reduced pressure
  6. filtrationthe insoluble solid was recovered by filtration
  7. washwashed repeatedly with water
  8. customdried under vacuum on phosphorous pentoxyde

Sources & evidence

ORD record
ord-f60ad16b73454356a0502e513cf14ef9
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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