Hydrochloric Acid → 4-(2-Aminopyridin-4-yl)benzaldehyde

HRID 1245476Notes

Reaction equation

HRID 1245476 reaction equation
Cl.[CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16]C(=O)OC(C)(C)C)[CH:11]=2)=[CH:6][CH:5]=1)=[O:3]>CCOC(C)=O>[NH2:16][C:12]1[CH:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH:2]=[O:3])=[CH:5][CH:6]=2)[CH:15]=[CH:14][N:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21912851Carbamic acid, (4-(4-formylphenyl)-2-pyridinyl)-, 1,1-dimethylethyl ester

Product 1

HCID 219128544-(2-Aminopyridin-4-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stream of HCl gas was bubbled into a suspension of tert-butyl 4-(4-formylphenyl)pyridin-2-ylcarbamate (2-1, 486 mg, 1.63 mmol) in EtOAc (50 mL) at 0° C. for 2 min. The acidified solution was allowed to reach 23° C. and was then stirred for 18 h. The reaction mixture was concentrated to give 4-(2-aminopyridin-4-yl)benzaldehyde (2-2) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 10.07 (s, 1H), 8.18 (d, 1H, J=5.5 Hz), 7.97 (d, 2H, J=8.6 Hz), 7.74 (d, 2H, J=8.1 Hz), 6.91 (dd, 1H, J=5.5, 1.5 Hz), 6.73 (s, 1H), 4.61 (s, 2H).

Workup

  1. customto reach 23° C.
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-1468c063090a4f57a5c08feb29b8bcbe
Source dataset
uspto-grants-2006_10
Patent number
US07125888B2

Reaction notes

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