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Hydrochloric Acid → 4-[(1-Ethylpropyl)amino]-3-nitrobenzoic acid

HRID 1750195
Notes
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Reaction equation

HRID 1750195 reaction equation
C([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[C:7]([N+:17]([O-:19])=[O:18])[CH:6]=1)C.C1COCC1.[OH-].[Na+].Cl>C(O)C>[CH2:13]([CH:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:20])=[O:3])=[CH:6][C:7]=1[N+:17]([O-:19])=[O:18])[CH2:15][CH3:16])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86714408HCID 86714408, compound

Product 1

HCID 115143484-[(1-Ethylpropyl)amino]-3-nitrobenzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

30.0 g of 4-(1-ethyl-propylamino)-3-nitro-benzoic acid ethyl ester were dissolved in 100 ml ethanol and 10 ml THF and 107 ml of 2 M aqueous sodium hydroxide solution were added. After stirring at room temperature over night, the reaction mixture was brought to pH 1 by addition of 2 M aqueous hydrochloric acid and extracted with ethyl acetate three times. The combined organic phases were dried over magnesium sulphate and concentrated to yield 27.0 g (100%) of 4-(1-ethyl-propylamino)-3-nitro-benzoic acid as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialThe combined organic phases were dried over magnesium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b6b6f9098bd14ff3acd106fe44f0f4bf
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09156796B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes