Ammonia → HCID 53716583, compound

Temperature

130 °C

A mixture of 6hydroxy-5-nitronicotinic acid (1.33 g, 7.22 mmol), phosphorus pentachloride (1.5 g, 7.20 mmol, 1.0 eq), and phosphorus oxychloride (2.7 mL) was heated at 130° C. under nitrogen for 4 hours. The resultant solution was concentrated via evaporation under reduced pressure. The residual oil [presumed to be 6-chloro-5-nitronicotinic acid, acid chloride] was dissolved in a solution of tetrahydrofuran and methylene chloride (1:1, 20 mL), and this solution was cooled to -78° C. A solution of ammonia in THF (2.7M, 15 mL, 40 mmol, 5 eq) was added dropwise, and the resultant reaction solution was allowed to warm to room temperature. Water (50 mL) was then added, and the aqueous mixture was extracted with methylene chloride (2×50 mL). The extracts were combined, dried (Na2SO4), and evaporated under reduced pressure to afford the title compound (0.72 g, 3.57 mmol, 49%) as a yellow solid: 1H NMR (CD3OD) δ 9.05 (d, J=2.2 Hz, 1H), 8.81 (d, J=2.2 Hz, 1H), 4.88 (s, 2 exchangeable H); 13C NMR (CD3OD) δ 166.7, 152.5, 146.1, 135.0, 131.3; HRMS calculated for C6H4ClN3O3 200.9942, found 200.9938. Anal. calcd for C6H4ClN3O3 ; C, 35.75; H, 2.00; N, 20.85. Found: C, 35.41; H. 2.14; N, 20.29 .

1. concentrationThe resultant solution was concentrated via evaporation under reduced pressure
2. dissolutionThe residual oil [presumed to be 6-chloro-5-nitronicotinic acid, acid chloride] was dissolved in a solution of tetrahydrofuran and methylene chloride (1:1, 20 mL)
3. temperaturethis solution was cooled to -78° C
4. customthe resultant reaction solution
5. temperatureto warm to room temperature
6. extractionthe aqueous mixture was extracted with methylene chloride (2×50 mL)
7. dry with materialdried (Na2SO4)
8. customevaporated under reduced pressure

ORD record

ord-b5916457d90e415b962a886b3028e0aa

Source dataset

uspto-grants-1999_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05886008