Triethylamine → Phthalimide

HRID 1388569Notes

Reaction equation

HRID 1388569 reaction equation
NC1(OC2C=CC=C(C(F)(F)F)C=2)C2N=CC=C(C)C=2C=C(OC)C1.ICCCC([N:32]1[C:36](=[O:37])[C:35]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:34]2[C:33]1=[O:42])C.IC(N1C(=O)C2=CC=CC=C2C1=O)CCCC.C(N(CC)CC)C>C(OCCO)C.C(Cl)Cl>[C:36]1(=[O:37])[NH:32][C:33](=[O:42])[C:34]2=[CH:41][CH:40]=[CH:39][CH:38]=[C:35]12

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 6000781H-Isoindole-1,3(2H)-dione, 2-(4-iodo-1-methylbutyl)-HCID 70506124HCID 70506124, compoundHCID 70511798HCID 70511798, compound

Product 1

HCID 6809PhthalimideYield 79%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 8-amino-6-methoxy-4-methyl-8-(3-trifluoromethylphenoxy)quinoline (5.26 g, 15 mmol), 1-iodo-4-phthalimidopentane (5.26 g, 15 mol) in 2-ethoxyethanol (25 mL) was heated at 110° for 1.5 hour after which time an additional 7.5 mmol of iodophthalimidopentane and triethylamine were added. After stirring 1.5 hour an additional 7.5 mmol of each reagent was added. After stirring an additional 4.5 hours the reaction mixture was diluted with CH2Cl2 and the organic layer was washed with water (×3). After drying (K2CO3) the organic layer was concentrated to dryness and the residue was chromatographed over a silica gel column (33 mm×500 mm). Elution with chloroform afforded the intermediate phthalimide (6.65 g, 79%) which could be crystallized from EtOH to give mp 122°-124°.

Workup

  1. additionwere added
  2. additionwas added
  3. washthe organic layer was washed with water (×3)
  4. dry with materialAfter drying (K2CO3) the organic layer
  5. concentrationwas concentrated to dryness
  6. customthe residue was chromatographed over a silica gel column (33 mm×500 mm)
  7. washElution with chloroform

Sources & evidence

ORD record
ord-9d5c80d93d2144f3a3b5a5d70844adbd
Source dataset
uspto-grants-1984_02
Patent number
US04431807

Reaction notes

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