Hydrochloric Acid → HCID 13564462, compound

HRID 1284557Notes

Reaction equation

HRID 1284557 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.[F:14][C:15]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:16]=1[NH2:17].[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:17][C:16]1[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:15]=1[F:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 97092,4-DifluoroanilineHCID 4311764Sodium borohydrideHCID 13564460HCID 13564460, compound

Product 1

HCID 13564462HCID 13564462, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 6-hydroxy-3,4-dihydrobenzopyran-5-carboxaldehyde (299 mg, 1.68 mmol) and 2,4 -difluoroaniline (219 mg, 1.68 mmol) in methanol (8 mL) was heated to reflux for 20 minutes during which time the intermediate Schiff's base crystallized, and, after cooling to room temperature, was collected by filtration and dried. The isolated Schiff's base (175 mg, 36%) was suspended in methanol (8 mL) and sodium borohydride (25 mg, 0.66 mmol) was added. The mixture was stirred at room temperature for 5 minutes, poured into water (50 mL) and carefully neutralized (pH=7) with 2.5 N HCl. The product was collected by filtration and dried to afford 6-hydroxy-5-(2,4-difluorophenyl)aminomethyl-3, 4-dihydrobenzopyran, (170 mg, 96.6%), m.p. 120°-121° C.

Workup

  1. temperaturewas heated
  2. customcrystallized
  3. filtrationwas collected by filtration
  4. customdried
  5. filtrationThe product was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-a1974683faef44ccb8e4dad523e0aac3
Source dataset
uspto-grants-1986_01
Patent number
US04563476

Reaction notes

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