Methyl iodide → HCID 12800001, compound

HRID 2412626Notes

Reaction equation

HRID 2412626 reaction equation
Cl.[CH2:2]([CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:22]([OH:24])=[O:23])[CH:19]=2)[NH:14]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[OH-].[Na+].[CH3:27]I>C(O)(=O)C.O.C(O)C>[CH3:27][N:14]1[C:15]2[C:20](=[CH:19][C:18]([C:22]([OH:24])=[O:23])=[CH:17][CH:16]=2)[CH2:21][CH:13]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 3

HCID 6328Methyl iodide2×HCID 14798Sodium HydroxideHCID 24839540HCID 24839540, compound

Product 1

HCID 12800001HCID 12800001, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of (RS)-2-(n-undecyl)indoline-5-carboxylic acid hydrochloride (6.8 g), sodium hydroxide (6.8 g), water (25 ml), ethanol (75 ml) and methyl iodide (10 ml) was heated under reflux for 1 hour. Methyl iodide (5 ml) was added and the mixture was heated for 30 minutes, then poured into water and acidified with acetic acid. The product was collected and recrystallised from methanol to give (RS)-1-methyl-2-(n-undecyl)indoline-5-carboxylic acid (3.0 g), in the form of white needles, m.p. 102°-104° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. temperaturethe mixture was heated for 30 minutes
  4. customThe product was collected
  5. customrecrystallised from methanol

Sources & evidence

ORD record
ord-3e616c87d6dd42c39061dc0dc0a49091
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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