Hydrochloric Acid → HCID 22100464, compound

HRID 1457753Notes

Reaction equation

HRID 1457753 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:25][CH3:26])=[C:8]([CH:24]=1)[C:9]([NH:11][CH:12]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][C:17]([CH3:23])=[CH:18][CH:19]=2)[O:14][CH2:13]1)=[O:10].Cl>C(O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:25][CH3:26])=[C:8]([CH:24]=1)[C:9]([NH:11][CH:12]1[CH:21]([OH:22])[C:20]2[C:15](=[CH:16][C:17]([CH3:23])=[CH:18][CH:19]=2)[O:14][CH2:13]1)=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22100465HCID 22100465, compound

Product 1

HCID 22100464HCID 22100464, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.5 g (12.5 mmol) of sodium borohydride was introduced into a suspension of 8.65 g (25 mmol) of 3-(5-chloro-2-methoxybenzamido)-7-methyl-4-chromanone in 40 ml of ethanol. During stirring at 30°-40° C. for 2 hours, the solid dissolved. The solution was then cooled, introduced into ice/water and acidified to pH 1-2 with dilute hydrochloric acid. The precipitate was filtered off with suction, washed with water, dried and recrystallized from ethanol. The resulting 3-(5-chloro-2-methoxybenzamido)-7-methylchroman-4-ol (diastereomer mixture) had a melting point of 151°-152° C.

Workup

  1. dissolutionthe solid dissolved
  2. temperatureThe solution was then cooled
  3. filtrationThe precipitate was filtered off with suction
  4. washwashed with water
  5. customdried
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ebd9304c505c4f3ebb13652bb2ffe11b
Source dataset
uspto-grants-1998_12
Patent number
US05849755

Reaction notes

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