tert-Butanol → HCID 18979069, compound

HRID 2393094Notes

Reaction equation

HRID 2393094 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](C(O)=O)=[N:7]2.[C:17]([OH:21])([CH3:20])([CH3:19])[CH3:18].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.C([N:41]([CH2:44]C)CC)C>>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:41][C:44]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:29])=[N:7]2

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 99436352-Quinolinecarboxylic acid, 5-bromo-8-methoxy-

Product 1

HCID 18979069HCID 18979069, compound

Conditions

Temperature
80 °C

Procedure

5-Bromo-8-methoxyquinoline-2-carboxylic acid (2 g), t-butanol (25 ml) and triethylamine (1.48 ml) were combined under a nitrogen atmosphere and heated to 80° C. Diphenylphosphorylazide (2.29 ml) was added to the solution and heating was continued for 60 h by which time a white preciptate was present. The reaction mixture was evaporated in vacuo onto silica and purified by flash chromatography to give the title compound (1.21 g) as an off white solid.

Workup

  1. temperatureheating
  2. customThe reaction mixture was evaporated in vacuo onto silica
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-8fd8d820442340eda5fdae2f56b55428
Source dataset
uspto-grants-1998_09
Patent number
US05804588

Reaction notes

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