2-Bromo-3-nitrobenzoic acid → 2-(Cyclopropylamino)-3-nitrobenzoic acid

HRID 2036603Notes

Reaction equation

HRID 2036603 reaction equation
Br[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:14]1([NH2:17])[CH2:16][CH2:15]1>C1COCC1.CCOC(C)=O>[CH:14]1([NH:17][C:2]2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 684522-Bromo-3-nitrobenzoic acidHCID 69828Cyclopropylamine

Product 1

HCID 674315052-(Cyclopropylamino)-3-nitrobenzoic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-bromo-3-nitrobenzoic acid (1.0 g, 4.1 mmol), cyclopropanamine (0.85 mL, 12.2 mmol) in THF (10 mL) under N2 was heated at 60° C. for 1 day. The reaction mixture was diluted with EtOAc, washed with water, brine, and dried over magnesium sulfate. The organic phase was concentrated in vacuo. The residue, as a crude 2-(cyclopropylamino)-3-nitrobenzoic acid: LC-MS (ESI) m/z 223.0 [M+H]+. The crude product was subjected to the next reaction without further purification.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationThe organic phase was concentrated in vacuo
  4. customThe crude product was subjected to the next reaction without further purification

Sources & evidence

ORD record
ord-9decef73335d4f80b9997df994bf8f75
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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