Hydrochloric Acid → Ethyl 2-(aminomethyl)-5-fluorobenzoate hydrochloride

HRID 455291Notes

Reaction equation

HRID 455291 reaction equation
[ClH:1].C(OC([NH:9][CH2:10][C:11]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:12]=1[C:13]([O-:15])=[O:14])=O)(C)(C)C.[CH2:21]1COC[CH2:22]1>>[ClH:1].[NH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:12]=1[C:13]([O:15][CH2:21][CH3:22])=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 866675072-((Tert-butoxycarbonylamino)methyl)-5-fluorobenzoate

Product 1

HCID 67109674Ethyl 2-(aminomethyl)-5-fluorobenzoate hydrochloride

Conditions

Temperature
50 °C

Procedure

Concentrated HCl (37%; 16 ml) was added dropwise to a solution of thyl 2-((tert-butoxycarbonylamino)methyl)-5-fluorobenzoate (Example 3; 15.9 g; 53.6 mmol) in THF (96 ml). The mixture was heated at 50° C. for 2 hours. The mixture was concentrated to dryness. The residue was taken up in ethanol (200 ml) and concentrated again. The solid was triturated from ether (100 ml). The precipitate was filtered off and washed with diethyl ether (2×50 ml).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. concentrationconcentrated again
  3. customThe solid was triturated from ether (100 ml)
  4. filtrationThe precipitate was filtered off
  5. washwashed with diethyl ether (2×50 ml)

Sources & evidence

ORD record
ord-ebd0173aa2fb4a64ab8da0b4ff32eadb
Source dataset
uspto-grants-2013_07
Patent number
US08497270B2

Reaction notes

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