Sulfuric Acid → HCID 86723386, compound

HRID 508545Notes

Reaction equation

HRID 508545 reaction equation
[C:1]([C:5]1[C:10]([F:11])=[C:9]([NH:12]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:8]=[C:7]([CH:32](OCC)[O:33]CC)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].OS(O)(=O)=O.CC#N>O>[NH2:12][C:9]1[C:10]([F:11])=[C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])[N:6]=[C:7]([CH:32]=[O:33])[CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 86723383HCID 86723383, compound

Product 1

HCID 86723386HCID 86723386, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using the procedure for Example 12, 2-(tert-butyl)-6-(diethoxymethyl)-3-fluoro-N-tritylpyridin-4-amine (2461 mg, 4.8 mmol), conc H2SO4 (1 mL), CH3CN (35 mL) and H2O (35 mL) gave 4-amino-6-(tert-butyl)-5-fluoropicolinaldehyde (718 mg, 73.2%) as a white solid: mp 129-130° C.; 1H NMR (400 MHz, CDCl3) δ 9.86 (s, 1H), 7.26 (d, J=6.3 Hz, 2H), 4.37 (s, 2H), 1.43 (d, J=1.5 Hz, 9H); 13C NMR (101 MHz, CDCl3) δ 193.06, 149.83 (d, J=14.8 Hz), 148.90 (d, J=253.5 Hz), 148.71 (d, J=5.5 Hz), 141.32 (d, J=12.6 Hz), 107.56 (d, J=3.7 Hz), 33.32 (d, J=1.4 Hz), 21.85 (d, J=1.2 Hz), 13.90; 19F NMR (376 MHz, CDCl3) δ −137.45 (d, J=4.6 Hz); HRMS-ESI (m/z) [M+H]+ calcd for C10H13FN2O, 196.1012. found, 196.0994.

Sources & evidence

ORD record
ord-494a76b39ffc478486defbbcf81e65fa
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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