Ethanol → trans-N-(1,2,3,4-tetrahydro-4-hydroxy-1-naphthyl)acetamide

HRID 372394Notes

Reaction equation

HRID 372394 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([NH:12][C:13](=[O:15])[CH3:14])[CH2:4][CH2:3]1.C(O)C.[BH4-].[Na+]>O>[OH:1][C@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@H:5]([NH:12][C:13](=[O:15])[CH3:14])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 13037024N-(4-Oxo-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide

Product 1

HCID 70619274trans-N-(1,2,3,4-tetrahydro-4-hydroxy-1-naphthyl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 19.2 g. of N-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)acetamide and 275 ml. of absolute ethanol is stirred under a nitrogen atmosphere and 3.58 g. sodium borohydride added. The reaction mixture is stirred at room temperature for 16 hours, then 200 ml. of water is added and the stirring continued for 4 hours. Next, the reaction mixture is evaporated to dryness in vacuo and the residue treated with 250 ml. of water. The mixture is cooled in an ice bath and acidified with concentrated hydrochloric acid. The precipitated yellow solid is collected and dried; weight 6 g., m.p. 120°-127° C.

Workup

  1. additionA mixture of 19.2 g
  2. waitthe stirring continued for 4 hours
  3. customNext, the reaction mixture is evaporated to dryness in vacuo
  4. additionthe residue treated with 250 ml
  5. temperatureThe mixture is cooled in an ice bath
  6. customThe precipitated yellow solid is collected
  7. customdried

Sources & evidence

ORD record
ord-006a6a1cca414bedbf39015e808c184e
Source dataset
uspto-grants-1978_05
Patent number
US04091018

Reaction notes

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