Methane → HCID 14279607, compound

HRID 1722473Notes

Reaction equation

HRID 1722473 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 concentrated hydrochloric acid. The addition of 20 ml of methylene chloride caused the 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 concentrated 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-8bb2ac232fff4f7a9ad58b6f280fcdd1
Source dataset
uspto-grants-1989_08
Patent number
US04855448

Reaction notes

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