Azane;hydrate → HCID 59134312, compound

HRID 1993468Notes

Reaction equation

HRID 1993468 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[CH:8]=[C:7]3[O:13][C:14]([CH3:19])([CH3:18])[C@@H:15]4[O:17][C@@H:16]4[C:6]3=[CH:5][C:4]=2[N:3]=1.O.[NH3:21]>C(O)C>[NH2:21][C@H:16]1[C:6]2[C:7](=[CH:8][C:9]3[C:10]([CH3:12])=[CH:11][C:2]([Cl:1])=[N:3][C:4]=3[CH:5]=2)[O:13][C:14]([CH3:19])([CH3:18])[C@@H:15]1[OH:17]

Participants

4

Reactant 2

HCID 12896473Azane;hydrateHCID 25197113HCID 25197113, compound

Product 1

HCID 59134312HCID 59134312, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (3R*,4R*)-7-chloro-3,4-epoxy-2,2,9-trimethyl-3,4-dihydro-2H-pyrano[2,3-g]quinoline (2.0 g, 7.25 mmol) in ethanol (20 mL), ammonia water (10 mL) was added, and the resulting mixture was stirred in a sealed tube at 90° C. for 3 hours. Upon the completion of the reaction, the reaction solution was concentrated, and ethyl acetate was added thereto, The resulting solution was washed with water and then with saturated sodium chloride solution, and dried over magnesium sulfate and concentrated. The resulting mixture was purified by silica gel column (hexane/ethyl acetate=1/2) to obtain the aimed product (yield: 86%).

Workup

  1. customUpon the completion of the reaction
  2. concentrationthe reaction solution was concentrated
  3. additionethyl acetate was added
  4. washThe resulting solution was washed with water
  5. dry with materialwith saturated sodium chloride solution, and dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting mixture was purified by silica gel column (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-d35a63961dfc4a4a92eaafbdae4a57a9
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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