Water → HCID 24852911, compound

HRID 551787Notes

Reaction equation

HRID 551787 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([C:11]([O:13]C2C=CC([N+]([O-])=O)=CC=2)=O)[CH2:3][CH2:2]1.[NH:23]1[CH2:27][CH2:26][CH:25]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[CH2:24]1.O>ClCCl>[N:30]1[CH:31]=[CH:32][CH:33]=[C:28]([CH:25]2[CH2:26][CH2:27][N:23]([C:11]([N:4]3[C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[O:1][CH2:2][CH2:3]3)=[O:13])[CH2:24]2)[CH:29]=1

Participants

5

Reactant 3

HCID 962WaterHCID 36136513-(Pyrrolidin-3-yl)pyridineHCID 15425910HCID 15425910, compound

Product 1

HCID 24852911HCID 24852911, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

0.2 g of 4-nitrophenyl 2,3-dihydro-4H-1,4-benzoxazine-4-carboxylate, 0.1 g of 3-(pyrrolidin-3-yl)pyridine and 1.5 ml of water are introduced into a 10 ml glass tube. The tube is sealed and then heated at 100° C. under microwave irradiation for 35 minutes. Dichloromethane is added. The organic phase is dried over magnesium sulfate and the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel with a dichloromethane/methanol gradient from 1/0 to 95/5. 0.19 g of 4-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazine is obtained.

Workup

  1. customThe tube is sealed
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customthe solvent is evaporated under reduced pressure
  4. customThe residue is chromatographed on silica gel with a dichloromethane/methanol gradient from 1/0 to 95/5

Sources & evidence

ORD record
ord-8118ac423826498189df1a9ba1c21220
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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