Acetic Acid → HCID 13293071, compound

HRID 904820Notes

Reaction equation

HRID 904820 reaction equation
[C:1]([NH:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[CH:10][CH:11]=2)[C:6]1=[O:17])(=[O:3])[CH3:2].[BH4-].[Na+].C(O)(=O)C.CCOCC>C(O)C>[C:1]([NH:4][C@@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[CH:10][CH:11]=2)[C@H:6]1[OH:17])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 4311764Sodium borohydride2×HCID 13435388HCID 13435388, compound

Product 1

HCID 13293071HCID 13293071, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 2-acetamido-7-methoxy-3,4-dihydronaphthalen 1(2H)-one in absolute ethanol (100 ml) was added sodium borohydride (1.6 gms, 0.04 m) in portions. After stirring for 1/2 hour, acetic acid was added to decompose any excess sodium borohydride. The reaction mixture was poured onto water (150 ml) and this was extracted with ethyl acetate (3×150). The ethyl acetate was washed with aqueous saturated sodium chloride, and was dried over anhydrous sodium sulfate. After filtration, the ethyl acetate was removed under reduced pressure (20 mm) to give a semisolid. The solid was slurried with ether and filtered to yield 3.3 gms (35%) of product as a white solid, m.p. 135°-140° C.

Workup

  1. additionThe reaction mixture was poured onto water (150 ml)
  2. extractionthis was extracted with ethyl acetate (3×150)
  3. washThe ethyl acetate was washed with aqueous saturated sodium chloride
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe ethyl acetate was removed under reduced pressure (20 mm)
  7. customto give a semisolid
  8. filtrationfiltered

Sources & evidence

ORD record
ord-505e05079b074c3fb210d1b77d465fab
Source dataset
uspto-grants-1983_12
Patent number
US04420480

Reaction notes

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