Ethyl 2-aminobenzoate → HCID 57974155, compound

HRID 1362874Notes

Reaction equation

HRID 1362874 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:21]=[CH:20][CH:19]=[CH:18][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(N(CC)C(C)C)(C)C>C(O)(C)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][C:11]2[CH:21]=[CH:20][CH:19]=[CH:18][C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]([F:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6877Ethyl 2-aminobenzoateHCID 81531DiisopropylethylamineHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 57974155HCID 57974155, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A round-bottomed flask was charged with 2,4-dichloro-5-fluoropyrimidine (2.5 g, 15 mmol), ethyl 2-aminobenzoate (4.9 g, 30 mmol), N,N-diisopropylethylamine (5.2 mL, 3.9 g, 30 mmol) and isopropanol (50 mL). The flask was fitted with a reflux condenser and the mixture was heated to reflux and stirred for 18 h. After cooling the reaction mixture to room temperature a precipitate appeared. The solid was collected and washed sparingly with isopropanol then copiously with ethyl ether to afford the title compound as a white solid; yield, 1.8 g (41%). MS: M(C13H13ClFN3O2)=295.70 (M+H)+=296.0 and 298.0.

Workup

  1. customThe flask was fitted with a reflux condenser
  2. temperaturethe mixture was heated
  3. temperatureto reflux
  4. customThe solid was collected
  5. washwashed sparingly with isopropanol

Sources & evidence

ORD record
ord-817b9bf733c04b37afe114c642a99f73
Source dataset
uspto-grants-2011_02
Patent number
US07884098B2

Reaction notes

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