Hydrochloric Acid → Ethyl 4-amino-phenyloxyacetate hydrochloride

HRID 1459422Notes

Reaction equation

HRID 1459422 reaction equation
CC(C)(OC([NH:7][C:8]1[CH:20]=[CH:19][C:11]([O:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=1)=O)C.[ClH:22]>CCOC(C)=O>[ClH:22].[NH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54043329Ethyl 2-(4-{[(tert-butoxy)carbonyl]amino}phenoxy)acetate

Product 1

HCID 21697723Ethyl 4-amino-phenyloxyacetate hydrochlorideYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 500 mL round bottomed flask with a stirring bar and a gas dispersion tube was added ethyl (4-(1,1-dimethylethoxycarbonylamino)phenoxy)acetate (11.9 g, 40.29 mmol) and dry EtOAc. This solution was cooled in an ice bath and saturated with anhydrous HCl gas over 15 min. The resulting suspension was aged 30 min. at 0° C. The excess HCl was removed with a stream of argon and the EtOAc was removed in vacuo. The solid product was triturated with EtOAc, collected on a frit, and dried in vacuo at room temperature to give 7.33 g (78%) of ethyl 4-aminophenoxyacetate, hydrochloride as a white crystalline soild.

Workup

  1. customThe excess HCl was removed with a stream of argon
  2. customthe EtOAc was removed in vacuo
  3. customThe solid product was triturated with EtOAc
  4. customcollected on a frit
  5. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-fa4e98cec8b94a2aaa17a8b4eb09be32
Source dataset
uspto-grants-1998_12
Patent number
US05854245

Reaction notes

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