Sulfuric Acid → Tert-Butylamine

HRID 508566Notes

Reaction equation

HRID 508566 reaction equation
[C:1]([NH:5][C:6]1[CH:11]=[C:10]([CH:12](OCC)[O:13]CC)[N:9]=[C:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[C:7]=1[F:26])([CH3:4])([CH3:3])[CH3:2].OS(O)(=O)=O>CC#N.O>[C:1]([NH:5][C:6]1[C:7]([F:26])=[C:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[N:9]=[C:10]([CH:12]=[O:13])[CH:11]=1)([CH3:4])([CH3:2])[CH3:3].[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 1118Sulfuric AcidHCID 86723415HCID 86723415, compound

Product 2

HCID 6385Tert-ButylamineHCID 86723414HCID 86723414, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
78 °C

Procedure

A mixture of the N-tert-butyl-2-(4-chlorophenyl)-6-(diethoxymethyl)-3-fluoropyridin-4-amine (130 mg, 0.34 mmol) in CH3CN (1 mL) and H2O (1 mL) was treated with 1 M H2SO4 (0.5 mL) resulting in a light yellow solution. The reaction flask was placed in an oil bath and heated to 78° C. After 4 h, an aliquot of the reaction mixture was partitioned between EtOAc and 10% NaHCO3 and analyzed by HPLC. HPLC analysis showed that all of the starting material had been consumed and only a trace of the desired product formed (mainly aldehyde with t-butylamine still intact). After stirring for 20 h at 78° C., HPLC analysis still showed only a trace of the desired product (<2%). The reaction was stopped at this point.

Workup

  1. customresulting in a light yellow solution
  2. customThe reaction flask was placed in an oil bath
  3. customan aliquot of the reaction mixture was partitioned between EtOAc and 10% NaHCO3
  4. customhad been consumed

Sources & evidence

ORD record
ord-8e8ee5df69c3465e9abac1d328840aae
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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