N-Hydroxyphthalimide → HCID 22131438, compound

HRID 1271784Notes

Reaction equation

HRID 1271784 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:33]1[C:37](=[O:38])[C:36]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:35]2[C:34]1=[O:43].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[N:9]1[C:10]2[C:5](=[CH:4][C:3]([CH2:2][O:1][N:33]3[C:34](=[O:43])[C:35]4=[CH:42][CH:41]=[CH:40][CH:39]=[C:36]4[C:37]3=[O:38])=[CH:12][CH:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 15143856-HydroxymethylquinolineHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 22131438HCID 22131438, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(hydroxymethyl)quinoline (520 mg, 3.27 mmol), triphenyl phosphine (900 mg, 3.44 mmol, 1.05 equiv) and N-hydroxyphthalimide (560 mg, 3.43 mmol, 1.05 equiv) were dissolved in 25 mL of dry THF. Diethylazodicarboxylate (574 μL, 3.63 mmol, 1.11 equiv) was then added dropwise and the reaction was stirred overnight. The reaction mixture filtered to give a white solid. The filtrate was concentrated and a second crop of material was obtained by triturating with Et2O. This was combined with the original solid and recrystallization from EtOH gave the desired product (782 mg) as a fluffy white solid. MS(CI) m/e 305 (M+H)+.

Workup

  1. filtrationThe reaction mixture filtered
  2. customto give a white solid
  3. concentrationThe filtrate was concentrated
  4. customa second crop of material was obtained
  5. customby triturating with Et2O
  6. customThis was combined with the original solid and recrystallization from EtOH

Sources & evidence

ORD record
ord-4fb7ed63eca34d2da161169c8058260b
Source dataset
uspto-grants-2007_04
Patent number
USRE039591E1

Reaction notes

Loading…