Hydrochloric Acid → HCID 67095334, compound

HRID 2112082Notes

Reaction equation

HRID 2112082 reaction equation
[NH2:1][N:2]1[CH2:10][C:9]2[C:4](=[C:5]([N+:11]([O-:13])=[O:12])[CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:14].[CH2:15]([O:22][CH2:23][C:24](Cl)=[O:25])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(C(C)C)C(C)C)C.Cl>ClCCl.C1COCC1>[CH2:15]([O:22][CH2:23][C:24]([NH:1][N:2]1[CH2:10][C:9]2[C:4](=[C:5]([N+:11]([O-:13])=[O:12])[CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:14])=[O:25])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 177085Benzyloxyacetyl chlorideHCID 67095146HCID 67095146, compound

Product 1

HCID 67095334HCID 67095334, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

870 mg (4.5 mmol) 2-amino-7-nitro-2,3-dihydro-isoindol-1-one (prepared analogously to method 2) are dissolved in 82 ml dichloromethane and 64 ml THF. The solution is combined with 2.8 ml (3.3 eq, 20 mmol) benzyloxyacetyl chloride, 4.8 ml (28.0 mmol) N-ethyldiisopropyl-amine and 10 mg N,N-dimethylaminopyridine and stirred for 3 h at 25° C. Then the reaction mixture is combined with 100 ml aqueous 0.1 N hydrochloric acid and extracted three times with 50 ml of ethyl acetate. The organic phase is dried with magnesium sulphate, the solvent is eliminated in vacuo and the crude product is purified by chromatography. The carrier used is silica gel and the eluant used is a mixture of dichloromethane:methanol (95:5).

Workup

  1. extractionextracted three times with 50 ml of ethyl acetate
  2. dry with materialThe organic phase is dried with magnesium sulphate
  3. customthe crude product is purified by chromatography
  4. additiona mixture of dichloromethane:methanol (95:5)

Sources & evidence

ORD record
ord-f6f004048e4e487e92b3a5cea48622a4
Source dataset
uspto-grants-2009_04
Patent number
US07521457B2

Reaction notes

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