Hydrochloric Acid → HCID 13580474, compound

HRID 483098Notes

Reaction equation

HRID 483098 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=O.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[BH4-].[Na+].Cl>O.CO>[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH2:4][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 956952-Hydroxy-5-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 13580474HCID 13580474, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 15.2 g 2-hydroxy-5-methoxy benzaldehyde, 93 g of aniline and 100 ml of methanol was stirred at 25° for 20 hours. The mixture was then cooled with an ice-bath and stirred, and 3.9 g of sodium borohydride was added slowly. The mixture was stirred for 1 hour at 25°, 150 ml of water was added and the pH was adjusted to 7.0 with 2.5N hydrochloric acid. The resultant solid was collected, washed with water and purified by chromatography on silica gel using 3:17 ethyl acetate:n-hexane as an eluant. A 17.7 g yield of N-(2-hydroxy-5-methoxybenzyl)aniline was obtained. M.p. 82°-84°.

Workup

  1. temperatureThe mixture was then cooled with an ice-bath
  2. stirringstirred
  3. stirringThe mixture was stirred for 1 hour at 25°
  4. customThe resultant solid was collected
  5. washwashed with water
  6. custompurified by chromatography on silica gel using 3:17 ethyl acetate

Sources & evidence

ORD record
ord-10c7fe4b3cb4400ca82d4b90710ce000
Source dataset
uspto-grants-1986_03
Patent number
US04578390

Reaction notes

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