Pyruvic Acid → HCID 22616999, compound

HRID 1871600Notes

Reaction equation

HRID 1871600 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=O.[C:7]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH:23]=O)=[CH:15]1)([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)(=O)C>[C:7]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([C:23]2[CH:4]=[C:2]([C:1]([OH:6])=[O:5])[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=2)=[CH:15]1)([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8]

Participants

5

Reactant 3

HCID 1060Pyruvic AcidHCID 6115AnilineHCID 2764519tert-butyl 3-formyl-1H-indole-1-carboxylate

Product 1

HCID 22616999HCID 22616999, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
85 °C

Procedure

To a 500 mL round bottom flask was added 27.2 g (0.31 mol) of pyruvic acid (Lancaster), N-Boc-indole-3-carboxaldehyde (0.16 mol) and 200 mL of acetic acid. The reaction mixture was heated at 85° C. until all the solid material had dissolved (~30 min). Then aniline (0.31 mol) was added and the reaction mixture was stirred for 90 minutes at 85° C. The precipitate was filtered hot in a fritted funnel and washed with acetic acid (2×50 mL) and then with ether (2×50 mL). The solid filter cake was dried in vacuo to yield 2-(N-Boc-3-indolyl)-4-quinolinecarboxylic Acid (3-50% yield) of pure (>95%) material.

Workup

  1. dissolutionhad dissolved (~30 min)
  2. filtrationThe precipitate was filtered hot in a fritted funnel
  3. washwashed with acetic acid (2×50 mL)
  4. filtrationThe solid filter cake
  5. customwas dried in vacuo

Sources & evidence

ORD record
ord-017f7b9d061047e1b6ce26d6e6993af2
Source dataset
uspto-grants-2000_08
Patent number
US06103905

Reaction notes

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