Methyl iodide → HCID 12800006, compound

HRID 2412638Notes

Reaction equation

HRID 2412638 reaction equation
[CH2:1]([CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][C:19]([C:24]([OH:26])=[O:25])=[CH:20][CH:21]=2)[NH:16]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[OH-].[Na+].[CH3:29]I>O.CO>[CH3:29][N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[C:19]([C:24]([OH:26])=[O:25])[CH:18]=2)[CH2:23][CH:15]1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 12799975HCID 12799975, compound

Product 1

HCID 12800006HCID 12800006, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

(RS)-2-(n-Tetradecyl)indoline-6-carboxylic acid (10.5 g) and sodium hydroxide (5.0 g) were refluxed together in a mixture of water (30 ml) and methanol (70 ml) for 1.5 hours, then methyl iodide (5 ml) was added. Water (30 ml) was added and the mixture was refluxed for 1 hour. The mixture was filtered, and the filtrate was diluted with water and acidified with acetic acid. The product was collected and recrystallised from a mixture of methanol and ethanol to give (RS)-1-methyl-2-(n-tetradecyl)indoline-6-carboxylic acid (7.0 g) in the form of off-white crystals, m.p. 115°-118° C.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. filtrationThe mixture was filtered
  3. additionthe filtrate was diluted with water
  4. customThe product was collected
  5. customrecrystallised from a mixture of methanol and ethanol

Sources & evidence

ORD record
ord-bb74409f8a664b3c80003ded7d858f66
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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