Acetic Anhydride → HCID 89964206, compound

HRID 1844031Notes

Reaction equation

HRID 1844031 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][C:18]=3[C:19]([F:22])([F:21])[F:20])[C:9]2=[O:12])=[CH:4][C:3]=1[CH3:23].[C:24]([O-:27])(=O)[CH3:25].[K+].C(OC(=O)C)(=O)C.C1OCCOCCOCCOCCOCCOC1.C(O[N:60]=O)CC(C)C>C(Cl)(Cl)Cl>[C:24]([N:1]1[C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][N:8]([C:13]4[CH:14]=[N:15][CH:16]=[CH:17][C:18]=4[C:19]([F:22])([F:21])[F:20])[C:9]3=[O:12])=[CH:4][C:3]=2[CH:23]=[N:60]1)(=[O:27])[CH3:25]

Participants

7

Reactant 5

HCID 7918Acetic AnhydrideHCID 8053Isoamyl NitriteHCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 89964618HCID 89964618, compound

Product 1

HCID 89964206HCID 89964206, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

7-Amino-6-methyl-2-(4-(trifluoromethyl)pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one (I-72b: 300 mg, 1.11 mmol) in chloroform (10 mL) was reacted with potassium acetate (153 mg, 1.56 mmol), acetic anhydride (0.213 mL, 2.23 mmol), 18-crown-6-ether (59 mg, 0.223 mmol) and isoamylnitrite (0.33 mL, 2.46 mmol) for 24 hours to afford the crude product. Purification by column chromatography on silica gel (100% ethyl acetate) afforded 80 mg of the product (16.7% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (100% ethyl acetate)

Sources & evidence

ORD record
ord-4f75cb2560b84b278c43f14feb103123
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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