Acetic Acid → 4-[2-Hydroxy-3-(3,4-dimethoxyphenethylamino)-propoxy]-benzotriazole hydrochloride

HRID 67644Notes

Reaction equation

HRID 67644 reaction equation
[ClH:1].Cl.Cl.[NH2:4][C:5]1[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][C:6]=1[O:12][CH2:13][CH:14]([OH:29])[CH2:15][NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1.C(O)(=O)C.[N:34]([O-])=O.[Na+]>O>[ClH:1].[OH:29][CH:14]([CH2:15][NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1)[CH2:13][O:12][C:6]1[C:5]2[N:4]=[N:34][NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 205275092,3-Diamino-1-[2-hydroxy-3-(3,4-dimethoxyphenethylamino)-propoxy]-benzene trihydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 1784903364-[2-Hydroxy-3-(3,4-dimethoxyphenethylamino)-propoxy]-benzotriazole hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

14.1 g. 2,3-Diamino-1-[2-hydroxy-3-(3,4-dimethoxyphenethylamino)-propoxy]-benzene trihydrochloride are dissolved in 10 ml. water and 3.5 ml. glacial acetic acid, cooled to 5° C. and mixed with 2.07 g. sodium nitrite in 3.6 ml. water. The reaction mixture is then stirred for 2.5 hours at ambient temperature. The resultant sodium chloride is precipitated out by the addition of 480 ml. isopropanol. After filtration, the filtrate is evaporated, purified over a column of silica gel using methanol/ethyl acetate (2:1 v/v) as elution agent, mixed with ethereal hydrochloric acid and the hydrochloride so obtained is crystallized from ethanol. There are obtained 1.26 g. (10% of theory) 4-[2-hydroxy-3-(3,4-dimethoxyphenethylamino)-propoxy]-benzotriazole hydrochloride; m.p. 123°-124° C.

Workup

  1. additionmixed with 2.07 g
  2. customThe resultant sodium chloride is precipitated out by the addition of 480 ml
  3. filtrationAfter filtration
  4. customthe filtrate is evaporated
  5. custompurified over a column of silica gel
  6. washas elution agent
  7. additionmixed with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-5c6e7c4ddd17458c9b7958e09d737eb1
Source dataset
uspto-grants-1982_08
Patent number
US04346093

Reaction notes

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