Sodium Hydroxide → 4-Chloro-3-iodopyridin-2-amine

HRID 2373995Notes

Reaction equation

HRID 2373995 reaction equation
C(OC(=O)[NH:7][C:8]1[C:13]([I:14])=[C:12]([Cl:15])[CH:11]=[CH:10][N:9]=1)(C)(C)C.[OH-].[Na+]>Br.C1COCC1>[Cl:15][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([NH2:7])[C:13]=1[I:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59852886tert-Butyl (4-chloro-3-iodopyridin-2-yl)carbamate

Product 1

HCID 229365964-Chloro-3-iodopyridin-2-amineYield 93%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of (4-chloro-3-iodo-pyridin-2-yl)-carbamic acid tert-butyl ester (5.6 g, 15.8 mmol) in 48% hydrobromic acid was heated at 100° C. for 10 min to give a clear solution. The mixture was cooled, treated with crushed ice and made basic with 6 M NaOH. The precipitated product was collected by vacuum filtration, washed with H2O and sucked partially on the funnel to give a white solid. The product was dissolved in THF and the solution dried over MgSO4 and concentrated in vacuo to give the title compound (3.7 g, 93%) as a white solid. 1H NMR (DMSO-d6) δ 7.84 (d, 1H, J=5.1 Hz), 6.73 (d, 1H, J=5.6 Hz), 6.51 (br s, 2H); MS(ESI+): m/z 254.97 (M+H)+.

Workup

  1. customto give a clear solution
  2. temperatureThe mixture was cooled
  3. additiontreated with crushed ice
  4. filtrationThe precipitated product was collected by vacuum filtration
  5. washwashed with H2O
  6. customto give a white solid
  7. dry with materialthe solution dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d78ca016f2f445a2ad329a1aeaccda7e
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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