Hydrochloric Acid → Benzoic acid, 4-[(phenylamino)methyl]-

HRID 1501044Notes

Reaction equation

HRID 1501044 reaction equation
[C:1]1([NH:7][CH2:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+].O1CCCC1.Cl>O.CO>[C:1]1([NH:7][CH2:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 11579611Benzoic acid, 4-[(phenylamino)methyl]-, methyl ester

Product 1

HCID 888115Benzoic acid, 4-[(phenylamino)methyl]-Yield 82.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of methyl 4-((phenylamino)methyl)benzoate (800 mg, 3.2 mmol), lithium hydroxide monohydrate (72 mg, 3 mmol), tetrahydrofuran (6 mL), methanol (2 mL) and water (2 mL) was stirred at 20° C. for 2 hours. The mixture was acidified to pH=1 with concentrated hydrochloric acid and then extracted with ethyl acetate (15 mL×3). The combined organic phase was separated, dried by sodium sulfate and then filtered. The filtrate was concentrated in vacuo to give 4-((phenylamino)methyl)benzoic acid (600 mg, 80%). The product was used for the next step directly without further purification. LRMS (M+H+) m/z: calcd 227.09. found 227.

Workup

  1. extractionextracted with ethyl acetate (15 mL×3)
  2. customThe combined organic phase was separated
  3. dry with materialdried by sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-51e5a32e3c084517bc2ab8315aad7bea
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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