Potassium Hydroxide → HCID 66807183, compound

HRID 1844009Notes

Reaction equation

HRID 1844009 reaction equation
N[C:2]1[S:3][C:4]2[C:13]3[C:12](=[O:14])[NH:11][CH2:10][CH2:9][C:8]=3[CH:7]=[CH:6][C:5]=2[N:15]=1.N([O-])=O.[Na+].[PH2](O)=O.[OH-].[K+]>P(O)(O)O.C(OCC)(=O)C.O>[S:3]1[C:4]2[C:13]3[C:12](=[O:14])[NH:11][CH2:10][CH2:9][C:8]=3[CH:7]=[CH:6][C:5]=2[N:15]=[CH:2]1

Participants

8

Reactant 4

HCID 14797Potassium HydroxideHCID 4124402Phosphinic AcidHCID 23668193Sodium NitriteHCID 87158339HCID 87158339, compound

Product 1

HCID 66807183HCID 66807183, compoundYield 10.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 107909Phosphorous acidSolvent

Conditions

Temperature
0 °C

Procedure

2-Amino-7,8-dihydrothiazolo[4,5-h]isoquinolin-9(6H)-one (I-66b: 1.4 g, 0.006 mol) in orthophosphorous acid (30 mL) was heated at 40° C. when a clear solution was formed. This was followed by the addition of NaNO2 (2.64 g, 0.038 mol) and H2O (10 mL) at 0° C. The resulting reaction mass was stirred at 0° C. for 30 minutes and added hypo phosphorous acid (35 mL). The reaction mass was stirred at 0° C. for 2 hours. The reaction was monitored by TLC (100% ethyl acetate). The reaction mass was diluted with ice-water, basified with KOH solution to pH 10 and extracted using ethyl acetate. The organic layer was concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (60% ethyl acetate in hexane) afforded 130 mg of the product (10% yield). LCMS: 99.03%, m/z=205.1 (M+1)

Workup

  1. customwas formed
  2. customThe resulting reaction mass
  3. stirringThe reaction mass was stirred at 0° C. for 2 hours
  4. extractionextracted
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customto afford the crude product
  7. customPurification by column chromatography on silica gel (60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8606ffcbd26446519186f260e363ff3b
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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