2-Aminobenzyl alcohol → HCID 13564470, compound

HRID 1284560Notes

Reaction equation

HRID 1284560 reaction equation
[OH:1][C:2]1[C:3]([CH:12]=O)=[CH:4][C:5]2[O:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:11]=1.[NH2:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17][OH:18].[BH4-].[Na+]>CO>[OH:1][C:2]1[C:3]([CH2:12][NH:14][C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=2[CH2:17][OH:18])=[CH:4][C:5]2[O:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 214392-Aminobenzyl alcoholHCID 4311764Sodium borohydrideHCID 13560308HCID 13560308, compound

Product 1

HCID 13564470HCID 13564470, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-hydroxy-3,4-dihydrobenzopyran-7-carboxaldehyde (400 mg, 2.27 mmol) and o-aminobenzylalcohol 282 mg, 2.25 mmol) in methanol (30 mL) was brought to a gentle boil and the volume slowly concentrated to 10 mL. An additional portion of methanol (20 mL) was added and the above process repeated two times. The mixture was cooled (ice bath) and a few drops of water added to aid in the crystallization of the Schiff's base. This material (440 mg) was collected by filtration, redissolved in methanol (30 mL) and sodium borohydride (60 mg, 1.59 mmol) was added in portions. The color was discharged immediately and the mixture allowed to stir at room temperature for 10 minutes. The reaction mixture as concentrated to half its original volume then poured into water (35 mL). After acidification (pH=5) with 2N HCl the mixture was filtered, and the filtrate basified with 7% NaHCO3. The product, which precipitated, was collected by filtration and vacuum dried to afford 6-hydroxy-7-(2-hydroxymethylphenyl)aminomethyl-3,4-dihydrobenzopyran (300 mg, 46.8%), m.p. 141-142° C.

Workup

  1. concentrationthe volume slowly concentrated to 10 mL
  2. additionAn additional portion of methanol (20 mL) was added
  3. temperatureThe mixture was cooled (ice bath) and a few drops of water
  4. additionadded to aid in the crystallization of the Schiff's base
  5. filtrationThis material (440 mg) was collected by filtration
  6. dissolutionredissolved in methanol (30 mL)
  7. concentrationThe reaction mixture as concentrated to half its original volume
  8. additionthen poured into water (35 mL)
  9. filtrationAfter acidification (pH=5) with 2N HCl the mixture was filtered
  10. customThe product, which precipitated
  11. filtrationwas collected by filtration and vacuum
  12. customdried

Sources & evidence

ORD record
ord-a35e9d42692046299d24b73477c2e3ce
Source dataset
uspto-grants-1986_01
Patent number
US04563476

Reaction notes

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