Water → HCID 18968903, compound

HRID 398783Notes

Reaction equation

HRID 398783 reaction equation
CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:20]1(=[N:34]O)[C:33]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]=2[CH2:23][CH2:22][CH2:21]1.[OH2:36]>ClCCl>[O:36]=[C:20]1[NH:34][C:33]2[CH:32]=[CH:31][C:30]3[C:25]([C:24]=2[CH2:23][CH2:22][CH2:21]1)=[CH:26][CH:27]=[CH:28][CH:29]=3

Participants

6

Reactant 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 14812Phosphorus oxide (P4O10)HCID 348924HCID 348924, compound

Product 1

HCID 18968903HCID 18968903, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of methanesulfonic acid (25 ml) and phosphorus pentaoxide (5.2 g, 37 mmol) was heated at 90° C. for 3.5 h. The solution was cooled to 50° C. and 3,4-dihydro-2H-phenanthren-1-one-oxime (4.8 g, 23 mmol) was added. The solution was heated at 60° C. for 10 minutes and then at 80° C. for 3.5 hr. The hot reaction mixture was added to a mixture of ice (300 g) and water (100 ml). The precipitated solid was isolated by filtration, redissolved in dichloromethane (50 ml), dried (MgSO4) and evaporated in vacuo to afford a white product. Purification was achieved using column chromatography with silica gel (200 g) and a mixture of heptane and ethyl acetate (1:2) to afford 4.8 g of 4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepine.

Workup

  1. temperatureThe solution was heated at 60° C. for 10 minutes
  2. customThe precipitated solid was isolated by filtration
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customto afford a white product
  6. customPurification
  7. additiona mixture of heptane and ethyl acetate (1:2)

Sources & evidence

ORD record
ord-d9abd205facc46f289d8fc139e637204
Source dataset
uspto-grants-1998_10
Patent number
US05817654

Reaction notes

Loading…