Isoquinolin-7-amine → Methyl 2-(isoquinolin-7-ylamino)-4-methylpentanoate

HRID 600666Notes

Reaction equation

HRID 600666 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1.[N+](=[C:14]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:15]([O:17][CH3:18])=[O:16])=[N-]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[CH:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][CH:14]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:15]([O:17][CH3:18])=[O:16])[CH:11]=2)[CH:6]=[CH:7][N:8]=1

Participants

5

Reactant 2

HCID 14660277Isoquinolin-7-amineHCID 713307532-Diazonio-1-methoxy-4-methylpent-1-en-1-olate

Product 1

HCID 60126917Methyl 2-(isoquinolin-7-ylamino)-4-methylpentanoate

Reagents, catalysts & solvents 2

HCID 21674Acetic acid, rhodium(2+) saltCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

800 mg of rhodium(II) acetate (dimer) are added to a solution of 5.19 g (36.0 mmol) of 7-aminoisoquinoline and 5.47 g (35.0 mmol) of methyl 2-diazo-4-methylpentanoate in 200 ml of toluene, and the mixture is heated at 80° C. for 12 hours. The cooled reaction mixture is filtered, and the filtrate is evaporated. The residue is chromatographed on a silica-gel column with ethyl acetate as eluent, giving methyl 2-(isoquinolin-7-ylamino)-4-methylpentanoate as a yellowish solid; ESI 273.

Workup

  1. customThe cooled reaction mixture
  2. filtrationis filtered
  3. customthe filtrate is evaporated
  4. customThe residue is chromatographed on a silica-gel column with ethyl acetate as eluent

Sources & evidence

ORD record
ord-6c9496d5f5e94f30bd9246b0e0ff99f5
Source dataset
uspto-grants-2011_03
Patent number
US07902223B2

Reaction notes

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