Water → 1-(3-(4-nitro-1H-pyrazol-1-yl)propyl)indoline

HRID 624022Notes

Reaction equation

HRID 624022 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][CH:11]=O)[CH:8]=1)([O-:3])=[O:2].[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1.O>CC#N.C(Cl)Cl.CC(O)=O>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][CH2:11][N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)[CH:8]=1)([O-:3])=[O:2]

Participants

7

Reactant 3

HCID 962WaterHCID 10328IndolineHCID 630411263-(4-nitro-1H-pyrazol-1-yl)propanal

Product 1

HCID 867042081-(3-(4-nitro-1H-pyrazol-1-yl)propyl)indoline

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(4-nitro-1H-pyrazol-1-yl)propanal (722 mg, 4.27 mmol) in MeCN (7.0 mL) and DCM (5.0 mL), indoline (0.48 mL, 4.27 mmol) was added, followed by STAB (1.36 g, 6.40 mmol) and one drop of AcOH. The resulting yellow suspension was stirred at rt for 1 h 15 min, then water and DCM was added and the org. layer was separated. The aq. layer was extracted with DCM and the combined org. layers were washed with brine, dried (MgSO4), filtered and the solvent was removed under reduced pressure to yield 1-(3-(4-nitro-1H-pyrazol-1-yl)propyl)indoline as a yellow oil which was used without further purification in the next step. LC-MS conditions B: tR=0.76 min, [M+H]+=273.06.

Workup

  1. customlayer was separated
  2. extractionThe aq. layer was extracted with DCM
  3. washlayers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-05e355aab7d343b1ad51cd299d819323
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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