Hydrochloric Acid → N-(2-(1H-Indene-1-yl)ethyl)hydroxylamine

HRID 1534796Notes

Reaction equation

HRID 1534796 reaction equation
[CH:1]1([CH2:10][CH:11]=[N:12][OH:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([BH3-])#N.[Na+].CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.Cl.[NH4+].[OH-]>CO.O>[CH:1]1([CH2:10][CH2:11][NH:12][OH:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 14923Ammonium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 856179012-(1H-indene-1-yl)acetaldoxime

Product 1

HCID 19908298N-(2-(1H-Indene-1-yl)ethyl)hydroxylamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

2-(1H-indene-1-yl)acetaldoxime (50 mg, 0.29 mmol) was dissolved in methanol (15 ml) and treated with sodium cyanoborohydride (34 mg, 0.54 mmol). Methyl orange indicator (ca 1 mg) was added, and the pH of the mixture adjusted by addition of 1:1 conc. HCl:MeOH to maintain the indicator color slightly to the red side of the turning point. After ca 1 ml of the acid mixture had been added, the indicator remained red. The reaction was made basic with conc. NH4OH, and water was added. The mixture was extracted with ether and the ether layer was dried over sodium sulfate, filtered, and evaporated to dryness in vacuo to provide N-(2-(1H-indene-1-yl)-ethyl)hydroxylamine.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ether
  3. dry with materialthe ether layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-cdeca3a901b44f63bdb2a148663f4a0f
Source dataset
uspto-grants-1992_02
Patent number
US05091387

Reaction notes

Loading…