4-Phenylbutyric Acid → N-(4-nitrophenyl)isoindoline-2-carboxamide

HRID 624119Notes

Reaction equation

HRID 624119 reaction equation
NC1C=CC([NH:8][C:9]([N:11]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12]2)=[O:10])=CC=1.C1(CCCC(O)=[O:30])C=CC=CC=1.O.[OH:33][N:34]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O>[N+:34]([C:38]1[CH:37]=[CH:42][C:41]([NH:8][C:9]([N:11]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12]2)=[O:10])=[CH:40][CH:39]=1)([O-:33])=[O:30]

Participants

8

Reactant 5

HCID 47754-Phenylbutyric AcidHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 62231518N-(4-aminophenyl)isoindoline-2-carboxamide

Product 1

HCID 68754770N-(4-nitrophenyl)isoindoline-2-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-(4-aminophenyl)isoindoline-2-carboxamide (100 mg, 0.395 mmol), 4-phenylbutanoic acid (78 mg, 0.474 mmol), 1-hydroxybenzotriazole hydrate (66.5 mg, 0.434 mmol) and N-methylmorpholine (0.109 ml, 0.987 mmol) in N,N-dimethylformamide (1.771 ml) at room temperature was treated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (136 mg, 0.711 mmol). The mixture was stirred overnight and diluted with water (10 ml); the resulting suspension was filtered with water washes to give after drying product with an impurity. This solid was suspended in 2% methanol/dichloromethane and filtered to provide the title compound.

Workup

  1. filtrationthe resulting suspension was filtered with water
  2. customto give
  3. customafter drying product with an impurity
  4. filtrationfiltered

Sources & evidence

ORD record
ord-42a4c9cf6a484ac283009c3f3719d8e2
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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