Sodium Azide → HCID 85869868, compound

HRID 1181443Notes

Reaction equation

HRID 1181443 reaction equation
O.[CH:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:12]([OH:14])=O)[C:6]=2[CH:5]=[CH:4][N:3]=1.C(Cl)(=O)C(Cl)=O.[N-:21]=[N+:22]=[N-:23].[Na+]>ClCCl.CN(C)C=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:12]([N:21]=[N+:22]=[N-:23])=[O:14])[C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 3

HCID 33557Sodium AzideHCID 65578Oxalyl chlorideHCID 69523124Isoquinoline-5-carboxylic acid monohydrate

Product 1

HCID 85869868HCID 85869868, compoundYield 44%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Isoquinoline-5-carboxylic acid monohydrate (5.00 g, 26.2 mmol) was suspended in dichloromethane (200 ml) and N,N-dimethylformamide (5 drops) added. Oxalyl chloride (4.57 ml, 52 mmol) was then added and the reaction stirred for 7 h. The solvent and excess oxalyl chloride was then evaporated and the residue taken up in dichloromethane (200 ml). A solution of sodium azide (2.1 g, 32.3 mmol) and tetra-n-butylammonium bromide (850 mg) in water (50 ml) was then added in one portion and the mixture stirred for 20 min. The layers were separated and the aqueous phase extracted with more dichloromethane (100 ml). The combined organic phases were evaporated and the residue purified by flash column chromatography (eluant ethyl acetate-dichloromethane (1:4)) to give the title compound as a yellow solid (2.27 g, 44%).

Workup

  1. customThe solvent and excess oxalyl chloride was then evaporated
  2. stirringthe mixture stirred for 20 min
  3. customThe layers were separated
  4. extractionthe aqueous phase extracted with more dichloromethane (100 ml)
  5. customThe combined organic phases were evaporated
  6. customthe residue purified by flash column chromatography (eluant ethyl acetate-dichloromethane (1:4))

Sources & evidence

ORD record
ord-9baf64d6536d4ab58a56d81ff92ab0a5
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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