Ethyl Acetate → HCID 87158339, compound

HRID 1844008Notes

Reaction equation

HRID 1844008 reaction equation
[S-:1][C:2]#[N:3].[K+].[NH2:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][NH:12][C:13]2=[O:16])=[CH:8][CH:7]=1.BrBr.C(OCC)(=O)C>C(O)(=O)C>[NH2:3][C:2]1[S:1][C:15]2[C:14]3[C:13](=[O:16])[NH:12][CH2:11][CH2:10][C:9]=3[CH:8]=[CH:7][C:6]=2[N:5]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24408BromineHCID 516872Potassium thiocyanateHCID 131528447-Amino-1,2,3,4-tetrahydroisoquinolin-1-one

Product 1

HCID 87158339HCID 87158339, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
-10 °C

Procedure

Potassium thiocyanate (8.62 g, 0.088 mol) was added to a stirred solution of 7-amino-3,4-dihydroisoquinolin-1(2H)-one (I-66a: 1.8 g, 0.01 mol) in acetic acid (60 mL) at −10° C. and this was followed by the addition of bromine (5.33 g, 0.033 mol). The resulting reaction mass was stirred at −10° C. for 3 hours and further at room temperature overnight. The reaction was monitored by TLC (100% ethyl acetate). The reaction mass was diluted with ice water and filtered. The resulting mixture was basified at 0° C. using 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 (20% ethyl acetate in hexane) afforded 1.4 g of the product (58.33% yield).

Workup

  1. customThe resulting reaction mass
  2. filtrationfiltered
  3. customwas basified at 0° C.
  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 (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-0aa10102e7844c7dbdf18ca3a5db4310
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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