Sulfuric Acid → HCID 86723398, compound

HRID 508552Notes

Reaction equation

HRID 508552 reaction equation
C([O:3][CH:4](OCC)[C:5]1[CH:10]=[C:9]([NH:11]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:8]([F:31])=[CH:7][N:6]=1)C.OS(O)(=O)=O.CC#N>O>[NH2:11][C:9]1[C:8]([F:31])=[CH:7][N:6]=[C:5]([CH:4]=[O:3])[CH:10]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 86723399HCID 86723399, compound

Product 1

HCID 86723398HCID 86723398, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Following the procedure for Example 12, 2-(diethoxymethyl)-5-fluoro-N-tritylpyridin-4-amine (457 mg, 1 mmol), conc H2SO4 (0.2 mL), CH3CN (5 mL) and H2O (5 mL) gave 4-amino-5-fluoropicolinaldehyde (126 mg, 87%) as a white solid: mp 133-135° C.; 1H NMR (400 MHz, CDCl3) δ 9.90 (s, 1H), 8.34 (d, J=2.7 Hz, 1H), 7.36 (d, J=7.5 Hz, 1H), 4.47 (br s, 2H); 19F NMR (376 MHz, CDCl3) δ −144.44; HRMS-ESI (P/z) [M+H]+ calcd for C6H5FN2O, 140.0386. found, 140.0384.

Sources & evidence

ORD record
ord-0bcd65876c44453e970013069a31ee1e
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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