Sodium Hydroxide → HCID 13324715, compound

HRID 544140Notes

Reaction equation

HRID 544140 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]#[N:16])[CH:7]=[CH:6]2.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]#[N:16])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 13324712HCID 13324712, compound

Product 1

HCID 13324715HCID 13324715, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4.0 g (16.1 mmole) of 3-(5-methoxy-1-indolyl)benzonitrile of Example 9a in 160 ml glacial acetic acid under nitrogen at 15°-20° C. was treated with 3.14 g (49.9 mmole, 3.1 equivalents) sodium cyanoborohydride. The reaction mixture was permitted to warm to room temperature and stir overnight (about 16 hours). The resulting solution was poured over ice (200 ml), made basic using 50% NaOH (165 ml) and extracted with chloroform (350 ml total). The combined organic extracts were washed with water (400 ml), brine (400 ml), dried over Na2SO4, and concentrated to give 3.90 g (96.8%) of the crude indoline as an oil. Crystallization from hot ethyl acetate-hexane afforded 1.87 g (46.4% overall) of 3-(5-methoxy-1-indolinyl)benzonitrile, m.p. 92.5°-93.5° C.

Workup

  1. extractionextracted with chloroform (350 ml total)
  2. washThe combined organic extracts were washed with water (400 ml), brine (400 ml)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-aa037b5efc2e43c5a0bd5d59e057b906
Source dataset
uspto-grants-1984_05
Patent number
US04448784

Reaction notes

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