Benzyl Bromide → HCID 15341579, compound

HRID 1684533Notes

Reaction equation

HRID 1684533 reaction equation
[CH:1]([C@H:3]1[C@H:7]2[CH2:8][CH2:9][C:10]3[C:15]([N:6]2[C:5](=[O:17])[O:4]1)=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=3)=[CH2:2].C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C.CN(C)C=O>[CH2:24]([O:16][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:6]1[C:5](=[O:17])[O:4][C@@H:3]([CH:1]=[CH2:2])[C@H:7]1[CH2:8][CH2:9]2)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 15341577HCID 15341577, compound

Product 1

HCID 15341579HCID 15341579, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 10 g (0.043 mol) of trans-3-ethenyl-7-hydroxy-3,3a,4,5-tetrahydro-1H-oxazolo[3,4-a]quinolin-1-one (obtained in Step 2 of Example 1) and 12 g (0.086 mol) of potassium carbonate in 250 ml of acetonitrile and 50 ml of dimethylformamide are added 8.9 g (0.052 mol) of benzyl bromide. The mixture is stirred at 80° C. for 1 h then filtered while hot and washed with acetonitrile, and the filtrate is evaporated to dryness under reduced pressure. The residue is taken up in ethyl acetate and washed several times with water, and the organic phase is then dried over sodium sulphate and concentrated under reduced pressure. After recrystallization from diisopropyl ether, 12.8 g of product are obtained.

Workup

  1. filtrationthen filtered while hot and
  2. washwashed with acetonitrile
  3. customthe filtrate is evaporated to dryness under reduced pressure
  4. washwashed several times with water
  5. dry with materialthe organic phase is then dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customAfter recrystallization from diisopropyl ether, 12.8 g of product
  8. customare obtained

Sources & evidence

ORD record
ord-087a3b0250a1436abd85c1a79bc78371
Source dataset
uspto-grants-1997_06
Patent number
US05641785

Reaction notes

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