Hydrochloric Acid → HCID 13564462, 화합물

HRID 1284557노트

반응식

HRID 1284557 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 13564462HCID 13564462, 화합물수율 96.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-a1974683faef44ccb8e4dad523e0aac3
출처 데이터셋
uspto-grants-1986_01
특허 번호
US04563476

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