Hydrochloric Acid → 2-Pyridinamine, 4-phenyl-

HRID 1245471Notes

Reaction equation

HRID 1245471 reaction equation
Cl.[C:2]1([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14]C(=O)OC(C)(C)C)[CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O>[C:2]1([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH2:14])[CH:9]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21912853Tert-butyl 4-phenylpyridin-2-ylcarbamate

Product 1

HCID 1090142-Pyridinamine, 4-phenyl-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A stream of HCl gas was bubbled into a suspension of tert-butyl 4-phenylpyridin-2-ylcarbamate (1–2, 0.93 g, 3.4 mmol, 1 equiv) in EtOAc (50 mL) at 0° C. for 2 min. The acidified solution was then heated at 60° C. for 3 h. The reaction mixture was cooled then concentrated to give 4-phenylpyridin-2-amine (1-3) as an off-white solid. LRMS m/z (M+H) Calcd: 171.2, found 170.9.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationthen concentrated

Sources & evidence

ORD record
ord-451ca872e6c545a785a87abbcb333346
Source dataset
uspto-grants-2006_10
Patent number
US07125888B2

Reaction notes

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