Dichloromethane → 4-Amino-2-chloronicotinaldehyde

HRID 2104121Notes

Reaction equation

HRID 2104121 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:14]([CH:15]=[O:16])=[C:13]([NH:17]C(=O)OC(C)(C)C)[CH:12]=[CH:11][N:10]=1.ClCCl>CC(OC)(C)C>[NH2:17][C:13]1[C:14]([CH:15]=[O:16])=[C:9]([Cl:8])[N:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 52987944tert-Butyl (2-chloro-3-formylpyridin-4-yl)carbamate

Product 1

HCID 454898674-Amino-2-chloronicotinaldehyde

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
35 °C

Procedure

Trifluoroacetic acid (17.4 mL, 234 mmol) was added carefully to a stirred mixture of Boc aldehyde 1-4 (20 g, 78.1 mmol) and dichloromethane (60 mL) keeping the temperature below 25° C. The solution was warmed to 35° C., aged overnight (vigorous off-gassing) and then cooled to room temperature. 25 mL of MTBE was added and the resulting white slurry was aged for one hour, filtered, and the filter cake rinsed with MTBE (10 mL×2). Solid 1-5c TFA salt was dried under vacuum.

Workup

  1. customthe temperature below 25° C
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. washthe filter cake rinsed with MTBE (10 mL×2)
  5. dry with materialSolid 1-5c TFA salt was dried under vacuum

Sources & evidence

ORD record
ord-2731e34d623c428384e38f56d56f75ed
Source dataset
uspto-grants-2009_08
Patent number
US07576209B2

Reaction notes

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