Acetic Acid → Isopropanol hydrochloride

HRID 2393556Notes

Reaction equation

HRID 2393556 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][C:10](=[O:14])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][NH2:20].C(O)(=O)C.C([BH3-])#N.[Na+]>CO.C1COCC1>[CH3:9][CH:10]([OH:14])[CH3:11].[ClH:15].[ClH:15].[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]([NH:20][CH2:19][C:18]3[CH:21]=[CH:22][CH:23]=[C:16]([Cl:15])[CH:17]=3)[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 77802Benzenemethanamine, 3-chloro-HCID 5003444Sodium cyanoborohydrideHCID 113214437-Nitro-2-tetralone

Product 2

HCID 21912024Isopropanol hydrochlorideHCID 23298434HCID 23298434, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

7-Nitro-3,4dihydro-2-(1H)-naphthaleneone (1.50 g, 7.85 mmol), 3-chlorobenzylamine (4.70 ml, 39.3 mmol), acetic acid (6.0 ml), 4 Å molecular sieves (20 ml), THF (15 ml), and MeOH (15 ml) were introduced into a flask and cooled to 0° C. Sodium cyanoborohydride (0.99 g, 15.7 mmol) was added portionwise over a 5-minute period. The mixture was stirred for 14 hr, filtered through celite, and concentrated to a syrup. The mixture was made basic with 2N NaOH and extracted with ether (3×50 ml). The combined extracts were washed with water, dried over magnesium sulfate, filtered, concentrated and chromatographed over silica gel (3% methanol/methylene chloride). Treatment of the oil with IPA/HCl yielded 7-nitro-2-(((3-chlorophenyl)methyl)amino)-1,2,3,4-tetrahydronaphthalene hydrochloride: (1.34 g, 50%); M.S. (M+H)+ =317.

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated to a syrup
  3. extractionextracted with ether (3×50 ml)
  4. washThe combined extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed over silica gel (3% methanol/methylene chloride)

Sources & evidence

ORD record
ord-d26ceb059b3645f4989791330ed344af
Source dataset
uspto-grants-1998_09
Patent number
US05807886

Reaction notes

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