Potassium Hydroxide → 9-fluoro-7-nitro-2,3,3a,4-tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine

HRID 56106

Reaction equation

HRID 56106 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][C@H:2]1[CH2:3][OH:4].[OH-].[K+].[F:10][C:11]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[C:13](F)[C:12]=1F>CS(C)=O.O>[F:10][C:11]1[C:12]2[N:1]3[CH2:7][CH2:6][CH2:5][CH:2]3[CH2:3][O:4][C:13]=2[CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 640091L-ProlinolHCID 27827931,2,3-Trifluoro-5-nitrobenzene

Product 1

HCID 853655159-fluoro-7-nitro-2,3,3a,4-tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazineYield 93%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of prolinol (2.74 g, 27.11 mmol) and KOH (3.17 g, 56.47 mmol) in DMSO (30 mL) was added 1,2,3-trifluoro-5-nitrobenzene (4.00 g, 22.59 mmol) at rt. The reaction mixture was heated at 65° C. for 4 h. The mixture was diluted with water (150 mL) and extracted with CH2Cl2 (100 mL×2). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a yellow solid (5.00 g, 93%).

Workup

  1. extractionextracted with CH2Cl2 (100 mL×2)
  2. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8c62219b2a643498f25b0140522e236
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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