Kojic amine → HCID 178518283, compound

HRID 2236763Notes

Reaction equation

HRID 2236763 reaction equation
[NH2:1][CH2:2][C:3]1[O:4][CH:5]=[C:6]([OH:10])[C:7](=[O:9])[CH:8]=1.CO[CH:13]=[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([Br:24])[CH:22]=2)[C:17](=[O:25])[NH:16][C:15]1=[O:26]>CN(C)C=O>[Br:24][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[C:17](=[O:25])[NH:16][C:15](=[O:26])[C:14]2=[CH:13][NH:1][CH2:2][C:3]1[O:4][CH:5]=[C:6]([OH:10])[C:7](=[O:9])[CH:8]=1

Participants

4

Reactant 2

HCID 3841Kojic amineHCID 686927644-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dione

Product 1

HCID 178518283HCID 178518283, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-aminomethyl-5-hydroxy-pyran-4-one (106 mg, 0.75 mmole), 4 mL of N,N-dimethylformamide and 4-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dione (212 mg, 0.75 mmole) is stirred for one hour at ambient temperature. The reaction mixture is evaporated to dryness, dissolved in 7.5% methanol in chloroform passed through Florisil eluting with 7.5% methanol in chloroform. The eluate is evaporated, treated with acetonitrile, the resulting solid filtered and dried to give an off white solid, 220 mg, (75%), mp 293-7° C. dec; MS (ES+): m/z 391 (M+H).

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. dissolutiondissolved in 7.5% methanol in chloroform
  3. customThe eluate is evaporated
  4. additiontreated with acetonitrile
  5. filtrationthe resulting solid filtered
  6. customdried
  7. customto give an off white solid, 220 mg, (75%), mp 293-7° C. dec

Sources & evidence

ORD record
ord-ec7d58b6ef7949139f47d0bcd4081d7f
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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