7-Nitro-1-tetralone → 7-Nitro-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 1915415Notes

Reaction equation

HRID 1915415 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+]>CO>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2[OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 384457-Nitro-1-tetraloneHCID 4311764Sodium borohydride

Product 1

HCID 110087787-Nitro-1,2,3,4-tetrahydronaphthalen-1-olYield 80.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Nitro-3,4-dihydro-2H-naphthalen-1-one (200 mg, 1.05 mmol) was dissolved in methanol (5 mL) and NaBH4 ((78 mg, 2.05 mmol) was added in portions. The reaction was stirred at room temperature for 20 min and then concentrated and purified by column chromatography (10-50% ethyl acetate-hexanes) to yield 7-nitro-1,2,3,4-tetrahydro-naphthalen-1-ol (163 mg, 80%). 1H NMR (400 MHz, CD3CN) δ 8.30 (d, J=2.3 Hz, 1H), 8.02 (dd, J=8.5, 2.5 Hz, 1H), 7.33 (d, J=8.5 Hz, 1H), 4.76 (t, J=5.5 Hz, 1H), 2.96-2.80 (m, 2H), 2.10-1.99 (m, 2H), 1.86-1.77 (m, 2H); HPLC ret. time 2.32 min, 10-99% CH3CN, 5 min run.

Workup

  1. concentrationconcentrated
  2. custompurified by column chromatography (10-50% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-a8f71732b16e400aa74961ea79338b1a
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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