Ethylene Glycol → HCID 15591372, compound

HRID 1633141Notes

Reaction equation

HRID 1633141 reaction equation
C(C[CH2:4][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH3:16])=[C:8]1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)#N.[OH-:23].[Na+].[CH2:25]([OH:28])[CH2:26]O>O>[C:25]([CH2:26][CH2:4][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH3:16])=[C:8]1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)([OH:28])=[O:23]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 13362115HCID 13362115, compound

Product 1

HCID 15591372HCID 15591372, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(4-Cyanobutyl)-3-methyl-2-(3-pyridyl)-indole (578 mg) is heated at 185° for 0.5 hour with 450 mg of powdered NaOH and 5 ml of ethylene glycol; there is obtained, after pouring the reaction solution into 50 ml water, washing with ether, and adjusting the pH to 6 with 2 N HCl, an oily solid which crystallizes to give 1-(4-carboxybutyl)-3-methyl-2-(3-pyridyl)indole of Example 5 (m.p. 127°-129°).

Workup

  1. customthere is obtained
  2. washwashing with ether
  3. customan oily solid which crystallizes

Sources & evidence

ORD record
ord-ceb40cc96b19467881a4422c4dfd255c
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

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