Sodium Hydroxide → HCID 58337710, compound

HRID 1887457Notes

Reaction equation

HRID 1887457 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:11]([CH3:18])[C:12]2[CH:13]=[N:14][CH:15]=[N:16][CH:17]=2)[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.Cl[Sn]Cl.[OH-].[Na+]>O1CCOCC1.Cl>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([N:11]([CH3:18])[C:12]2[CH:17]=[N:16][CH:15]=[N:14][CH:13]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 58337652HCID 58337652, compound

Product 1

HCID 58337710HCID 58337710, compoundYield 113.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound 31 (224 mg, 0.902 mmol, 1.00 eq) was dissolved in dioxane (4.5 mL) and SnCl2 (856 mg, 4.51 mmol, 5.00 eq) dissolved in conc HCl (1.5 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 224 mg (63%) of a tan solid that was used subsequently without purification. 1H NMR (400 MHz, CDCl3) δ 8.67 (s, 1H), 8.44 (s, 2H), 6.11-6.10 (m, 1H), 6.09-6.07 (m, 1H), 6.07-6.04 (m, 1H), 5.46 (s, 2H), 3.23 (s, 3H); ES-MS [M+1]+: 219.2.

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-ff9e3dc2310843ab8b80ab203d088baa
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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