Hydrochloric Acid → HCID 13564461, compound

HRID 1284556Notes

Reaction equation

HRID 1284556 reaction equation
[OH:1][C:2]1[C:11]([CH:12]=O)=[C:6]2[CH2:7][CH2:8][CH2:9][O:10][C:5]2=[CH:4][CH:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][CH:16]=1.[BH4-].[Na+].Cl>CO.O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:11]=1[CH2:12][NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7468p-AminoacetophenoneHCID 4311764Sodium borohydrideHCID 13564460HCID 13564460, compound

Product 1

HCID 13564461HCID 13564461, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 6-hydroxy-3,4-dihydrobenzopyran-5- carboxaldehyde (308 mg, 1.73 mmol) and p-aminoacetophenone (236 mg, 1.73 mmol) in methanol (8 mL) was heated at reflux for one hour. The mixture was cooled to 15° at which time the intermediate Schiff's base crystallized. After filtration and drying a light orange product (221 mg, 43.3%) was obtained. This material was suspended in methanol (8 mL) and sodium borohydride (28 mg, 0.74 mmol) was added. After stirring at room temperature for ten minutes the mixture was poured into water (75 mL) and the resulting suspension neutralized (pH=7) with 2.5 N HCl. The product was collected by filtration and dried to afford 6-hydroxy-5-(4-acetylphenyl) aminomethyl-3,4-dihydrobenzopyran (170 mg, 76.6%), m.p. 213°-215° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for one hour
  3. customcrystallized
  4. filtrationAfter filtration
  5. dry with materialdrying a light orange product (221 mg, 43.3%)
  6. customwas obtained
  7. filtrationThe product was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-ad898f76f63a442397332ef8aa866be5
Source dataset
uspto-grants-1986_01
Patent number
US04563476

Reaction notes

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