Sodium Hydroxide → HCID 58337609, compound

HRID 1887449Notes

Reaction equation

HRID 1887449 reaction equation
[CH3:1][N:2]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=1)[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.Cl[Sn]Cl.[OH-].[Na+]>O1CCOCC1.Cl>[CH3:1][N:2]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 58337675HCID 58337675, compound

Product 1

HCID 58337609HCID 58337609, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound 16 (330 mg, 1.44 mmol, 1.00 eq) was dissolved in dioxane (7 mL) and SnCl2 (1.37 g, 7.22 mmol, 5.00 eq) dissolved in conc HCl (3 mL) was added dropwise over 15 min. After determination of completion by LCMS, the reaction was neutralized with 1N NaOH, filtered, diluted with water and extracted with CH2Cl2 (2×). The combined organics were dried (MgSO4), filtered and concentrated in vacuo to give 284 mg (99%) of a brown oil that was used subsequently without purification. 1H NMR (400 MHz, CDCl3) δ 8.16 (d, J=2.3 Hz, 1H), 7.99 (dd, J=4.2, 1.6 Hz, 1H), 7.24-7.17 (m, 2H), 7.01-6.95 (m, 1H), 6.32-6.28 (m, 2H), 6.27-6.23 (m, 1H), 5.08 (s, 2H), 3.19 (s, 3H); ES-MS [M+1]+: 200.2.

Workup

  1. additionwas added dropwise over 15 min
  2. filtrationfiltered
  3. additiondiluted with water
  4. extractionextracted with CH2Cl2 (2×)
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40bbfd1947d8495e9bd5c01260037e91
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

Loading…