Methane → HCID 14279607, compound

HRID 1722466Notes

Reaction equation

HRID 1722466 reaction equation
C([O:3][C:4](=[O:29])[CH:5]([CH2:11][C:12]1[C:20]2[C:15](=[C:16]([C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)[C:6]([O:8]CC)=[O:7])C.C>[OH-].[Na+]>[C:21]([C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[NH:14][CH:13]=[C:12]2[CH2:11][CH:5]([C:6]([OH:8])=[O:7])[C:4]([OH:29])=[O:3])(=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 297MethaneHCID 14279605HCID 14279605, compound

Product 1

HCID 14279607HCID 14279607, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 10.0 g (0.025 mole) of 2-[(7-benzoyl-1H-indol-3-yl)methyl]propanedioic acid diethyl ester in 150 ml of 3N sodium hydroxide was heated at reflux for 18 hr, then treated with charcoal, cooled and filtered. The dark yellow filtrate was acidified by the dropwise addition of 50 ml of concentration hydrochloric acid. The addition of 20 ml of methylene chloride caused by formation of a ppt., which was collected and recrystallized from chloroform-methanol to give 6.0 g (70%) of off-white crystals, m.p. 188°-189° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hr
  3. temperaturecooled
  4. filtrationfiltered
  5. additionThe dark yellow filtrate was acidified by the dropwise addition of 50 ml of concentration hydrochloric acid
  6. additionThe addition of 20 ml of methylene chloride
  7. custom, which was collected
  8. customrecrystallized from chloroform-methanol

Sources & evidence

ORD record
ord-e3d23228fc9642f6a6353f8b931d715f
Source dataset
uspto-grants-1989_08
Patent number
US04855447

Reaction notes

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