2-Amino-4-chloropyridine → HCID 23153342, compound

HRID 492718Notes

Reaction equation

HRID 492718 reaction equation
[NH2:1][C:2]1C=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:12][CH:11]=1.Cl.[N:28]1C=CC=CC=1.C(OCC)(=O)C.CCCCCC>C(OCCO)C>[NH2:1][C:2]1[N:28]=[C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 5818662-Amino-4-chloropyridineHCID 10176127Pyridinium chlorideHCID 11253521Benzyl N-(4-aminophenyl)carbamateHCID 21226206Ethyl acetate hexane

Product 1

HCID 23153342HCID 23153342, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
120 °C

Procedure

2-Amino-4-chloropyridine (257 mg) was dissolved in 2-ethoxyethanol (10 ml), and then benzyl N-(4-aminophenyl)carbamate (533 mg) and pyridine hydrochloride (462 mg) were added thereto, followed by stirring at 120° C. overnight. The reaction mixture was cooled down to room temperature, and partitioned between ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate, then ethyl acetate:methanol=95:5). Fractions containing the target compound were concentrated to give a residue, to which ethyl acetate-hexane was then added to precipitate crystals. The solid was filtered, and dried under aeration to provide the titled compound (321.5 mg, 48%) as pale brown crystals.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. custompartitioned between ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under a reduced pressure
  6. customto give a residue, which
  7. customwas then purified by silica gel column chromatography (Fuji Silysia NH, eluent
  8. additionFractions containing the target compound
  9. concentrationwere concentrated
  10. customto give a residue
  11. customto precipitate crystals
  12. filtrationThe solid was filtered
  13. customdried under aeration

Sources & evidence

ORD record
ord-b400d48eb31747589a55df947397c8d6
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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