2-Amino-4-chlorobenzoic acid → HCID 178518014, compound

HRID 351402Notes

Reaction equation

HRID 351402 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(O)(=O)C.[CH:16](N)=[NH:17].C(OC(O)C)C>C(OCC)C>[Cl:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4]([OH:5])=[N:17][CH:16]=[N:1]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 666462-Amino-4-chlorobenzoic acidHCID 160693Formamidine acetateHCID 101298981-Ethoxyethanol

Product 1

HCID 178518014HCID 178518014, compoundYield 130.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Amino-4-chloro-benzoic acid (1.00 g, 11.7 mmol, 1.0 eq.), formamidine acetate (3.64 mL, 35.0 mmol, 3 eq.), and ethoxyethanol (20 mL) were refluxed under nitrogen overnight. Cooled to rt. Added 25 mL of diethyl ether. Solids precipitated. Filtered off solids. Pumped under high vacuum to give 2.75 g of white solids as product. LCMS detects (M+H)+=181.

Workup

  1. customSolids precipitated
  2. filtrationFiltered off solids

Sources & evidence

ORD record
ord-383d17361db24aa9b9478a8a6eea84ee
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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