Peracetic Acid → HCID 86706667, compound

HRID 2171003Notes

Reaction equation

HRID 2171003 reaction equation
C(OO)(=[O:3])C.[Cl:6][C:7]1[C:16]2[C:11](=[CH:12][N:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][N:8]=1.S(OS([O-])=O)([O-])=O.[Na+].[Na+].[OH-].[Na+]>C(OCC)(=O)C.O.C(O)(=O)C>[Cl:6][C:7]1[C:16]2[C:11](=[CH:12][N+:13]([O-:3])=[CH:14][CH:15]=2)[CH:10]=[CH:9][N:8]=1

Participants

8

Reactant 4

HCID 6585Peracetic AcidHCID 14798Sodium HydroxideHCID 24346Disodium disulfiteHCID 128847741-Chloro-2,6-naphthyridine

Product 1

HCID 86706667HCID 86706667, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under stirring, 205 ml (1.2 mol) peracetic acid (39% solution in acetic acid) was added to a solution of 98.8 g (0.60 mol) 1-chloro-[2,6]naphthyridine in 500 ml ethyl acetate and the mixture was stirred 18 hours at room temperature. The reaction mixture was diluted with water and acetic acid, treated with portions of sodium disulfite under stirring until a peroxide test was negative. Then the mixture was adjusted to pH value of 8 with aqueous NaOH. The solids were filtered off, washed with water and dried yielding 1-chloro-[2,6]-naphthyridine 6-oxide as slightly yellow crystals. The organic phase of the filtrate was separated, dried over sodium sulfate and evaporated. The residue was crystallized from tert-butyl-methyl-ether yielding another crop of product. HPLC/MS (A): 1.16 min, [M+H] 181.

Workup

  1. stirringthe mixture was stirred 18 hours at room temperature
  2. filtrationThe solids were filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-bf55b0d2bc2f4adcb5ea6968a7369311
Source dataset
uspto-grants-2015_06
Patent number
US09051318B2

Reaction notes

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