Hydrochloric Acid → N-[2-(Hydroxymethyl)-3,4-dihydro-2H-1-benzopyran-6-yl]acetamide

HRID 1906885Notes

Reaction equation

HRID 1906885 reaction equation
O1CCCCC1[O:7][CH2:8][CH:9]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]([NH:19][C:20](=[O:22])[CH3:21])[CH:17]=[CH:18][C:11]=2[O:10]1.CO.Cl>O>[OH:7][CH2:8][CH:9]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]([NH:19][C:20](=[O:22])[CH3:21])[CH:17]=[CH:18][C:11]=2[O:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 20211054N-[3,4-dihydro-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]-2H-1-benzopyran-6-yl]-acetamide

Product 1

HCID 22471897N-[2-(Hydroxymethyl)-3,4-dihydro-2H-1-benzopyran-6-yl]acetamideYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 27 parts of N-[3,4-dihydro-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]-2H-1-benzopyran-6-yl]-acetamide in 240 parts of methanol were added 100 parts of a hydrochloric acid solution 10% in water. The whole was stirred for 30 minutes at room temperature. The reaction mixture was evaporated till all traces of methanol were removed. After cooling, the product was filtered off from the aqueous phase, washed with water and crystallized from acetonitrile. The product was filtered off and dried, yielding 14.4 parts (74%) of N-[3,4-dihydro-2-(hydroxymethyl)-2H-1-benzopyran-6-yl]acetamide; mp. 156.5° C. (intermediate 12).

Workup

  1. customThe reaction mixture was evaporated till all traces of methanol
  2. customwere removed
  3. temperatureAfter cooling
  4. filtrationthe product was filtered off from the aqueous phase
  5. washwashed with water
  6. customcrystallized from acetonitrile
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-90bcded22ed44ceda0a7fd2ec326e645
Source dataset
uspto-grants-1987_03
Patent number
US04654362

Reaction notes

Loading…