Sodium Hydroxide → HCID 21873753, compound

HRID 639016Notes

Reaction equation

HRID 639016 reaction equation
Br[C:2]1[CH:3]=[C:4]2[O:16][CH2:15][CH2:14][O:13][C:5]2=[C:6]2[C:11]=1[NH:10][CH:9]=[CH:8][C:7]2=[O:12].[OH-].[Na+]>O.O1CCOCC1.[Pd]>[O:13]1[C:5]2=[C:6]3[C:11](=[CH:2][CH:3]=[C:4]2[O:16][CH2:15][CH2:14]1)[NH:10][CH:9]=[CH:8][C:7]3=[O:12]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21873662HCID 21873662, compound

Product 1

HCID 21873753HCID 21873753, compoundYield 114.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A suspension of 6-bromo-2,3-dihydro-7H-[1,4]dioxino[2,3-f]quinolin-10-one (3.4 g, 12 mmol) in water/dioxane (150 mL/80 mL) was treated with 1M aqueous sodium hydroxide solution then hydrogenated over 10% palladium on charcoal (1.5 g) for 20 hours. The mixture was filtered then acidified with 5M aqueous hydrochloric acid. On concentrating to ca 100 mL, a solid began to crystallise out. The mixture was stored at 5° C. overnight. Filtration and drying afforded a pale yellow solid (2.8 g, 100%). LC/MS (ES) m/z 203 (MH+ 92%); 1H-NMR (400 MHz, d6-DMSO), 11.4 (1H, s, NH), 7.64 (1H, d, J=7.2, CHNHC), 7.15 (1H, d, J=9.2, CHCO), 6.95 (1H, d, J=8.8, CHCN), 5.80 (1H, d, J=7.2, CH═CO), 4.26-4.27 (4H, m, 2×(CH2O)).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationOn concentrating to ca 100 mL
  3. customto crystallise out
  4. filtrationFiltration
  5. customdrying

Sources & evidence

ORD record
ord-8a31f9cbe0334ab5b718bafd3db4919e
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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