Hydrochloric Acid → Methyl 5-(aminomethyl)-2-chlorobenzoate--hydrogen chloride (1/1)

HRID 1469719Notes

Reaction equation

HRID 1469719 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([Cl:20])=[C:14]([CH:19]=1)[C:15]([O:17][CH3:18])=[O:16])=O)(C)(C)C.Cl>CCOC(C)=O>[ClH:20].[NH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([Cl:20])=[C:14]([CH:19]=1)[C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86692228Methyl 5-[(tert-butoxycarbonylamino)methyl]-2-chloro-benzoate

Product 1

HCID 66524840Methyl 5-(aminomethyl)-2-chlorobenzoate--hydrogen chloride (1/1)Yield 202.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 5-(((tert-butoxycarbonyl)amino)methyl)-2-chlorobenzoate (100 mg, 0.334 mmol) in EtOAc saturated with HCl (1 mL) was stirred at rt for 2 h. The reaction mixture was concentrated and was triturated with pentane to afford 80 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.20 (br s, 3H), 7.95 (s, 1H), 7.67 (s, 2H), 4.00 (s, 2H), 3.88 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customwas triturated with pentane

Sources & evidence

ORD record
ord-9cd1b63ca4714484986fcf1022f46188
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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