N-Hydroxysuccinimide → HCID 20393619, compound

HRID 1862816Notes

Reaction equation

HRID 1862816 reaction equation
O.[N:2]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[C:15]([OH:17])=[O:16])=[N+:3]=[N-:4].O[N:19]1[C:23](=[O:24])[CH2:22][CH2:21][C:20]1=[O:25]>CN(C=O)C>[N:2]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[C:15]([O:17][N:19]1[C:23](=[O:24])[CH2:22][CH2:21][C:20]1=[O:25])=[O:16])=[N+:3]=[N-:4]

Participants

4

Reactant 2

HCID 80170N-HydroxysuccinimideHCID 86736631HCID 86736631, compound

Product 1

HCID 20393619HCID 20393619, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Azido-3-quinolinic acid monohydrate (2.3 g; 0.01 M) was suspended at ambient temperatures in dry DMF (25 ml). N-hydroxysuccinimide (1.2 g; 0.01 M) was added and the resulting mixture cooled to 0°-5° C. N,N-dicyclohexylcarbodi-imide (2.3 g; 0.11 M) was added and the mixture stirred at 0°-5° C. for 1/2 hr. then at ambient temperatures for 4 days. The insoluble material was removed by filtration and the filtrate evaporated to dryness in vacuo. The residual solid was recrystallized from iso-propyl alcohol as a light-brown, crystalline solid, 2.5 g. (80%), m.p. 173°-5° C. (dec.)(Found: C, 53.71; H, 2.80; N, 22.47%. C14H9N5O4 requires: C, 54.02; H, 2.89; N, 22.47%), νmax (KBr), 2120, 1790, 1760, 1730, 1490, 1390, 1370, 1202, 890, 780, 640cm-1, δ[(CD3)2SO] 2.9(s)(CH2CH2), 7.57-8.4(m), 9.18(s) (aromatic protons), m/e 311(M+)

Workup

  1. temperaturethe resulting mixture cooled to 0°-5° C
  2. waitthen at ambient temperatures for 4 days
  3. customThe insoluble material was removed by filtration
  4. customthe filtrate evaporated to dryness in vacuo
  5. customThe residual solid was recrystallized from iso-propyl alcohol as a light-brown, crystalline solid, 2.5 g

Sources & evidence

ORD record
ord-8584d7e16b5a41b0a3f278ac16d76fbd
Source dataset
uspto-grants-1979_09
Patent number
US04166817

Reaction notes

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