Triethylamine → HCID 66777974, compound

HRID 878464Notes

Reaction equation

HRID 878464 reaction equation
Cl[C:2](=[O:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].[Br:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[C:17]([N+:22]([O-:24])=[O:23])[CH:16]=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[Br:14][C:15]1[CH:21]=[CH:20][C:18]([NH:19][C:2](=[O:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:17]([N+:22]([O-:24])=[O:23])[CH:16]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 701324-Bromo-2-nitroanilineHCID 4586585Methyl 8-chloro-8-oxooctanoate

Product 1

HCID 66777974HCID 66777974, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 8-chloro-8-oxooctanoate (229 mg, 1.11 mmol) in DMF at 0° C. was added a solution of 4-bromo-2-nitroaniline (200 mg, 0.922 mmol) and triethylamine (0.37 mL, 2.77 mmol) in DMF drop-wise. The reaction was stirred overnight at room temperature, diluted with ethyl acetate and washed with 1 N HCl, saturated sodium bicarbonate solution and brine. The separated organic layer was concentrated and purified by biotage column chromatography to give methyl 8-(4-bromo-2-nitrophenylamino)-8-oxooctanoate (290 mg)

Workup

  1. washwashed with 1 N HCl, saturated sodium bicarbonate solution and brine
  2. concentrationThe separated organic layer was concentrated
  3. custompurified by biotage column chromatography

Sources & evidence

ORD record
ord-2c2e60004d7a47e4aa128f640c755499
Source dataset
uspto-grants-2015_03
Patent number
US08987468B2

Reaction notes

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