Acetic Acid → HCID 22277855, compound

HRID 1063876Notes

Reaction equation

HRID 1063876 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:11])[C:9]=1[OH:10])[CH:5]=O.Cl.[CH2:13]([O:20][NH2:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([BH3-])#N.[Na+].[C:26](O)(=[O:28])C>N1C=CC=CC=1>[CH2:13]([O:20][N:21]([CH2:5][C:4]1[CH:3]=[C:2]([Cl:1])[C:9]([OH:10])=[C:8]([Cl:11])[CH:7]=1)[CH:26]=[O:28])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 168393,5-Dichloro-4-hydroxybenzaldehydeHCID 102312Benzyloxyamine hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 22277855HCID 22277855, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3,5-dichloro-4-hydroxybenzaldehyde (2.00 g, 10.5 mmol) and O-benzylhydroxylamine hydrochloride (1.84 g, 11.55 mmol) in 5 ml of pyridine was stirred for 2 h. All volatiles were removed in vacuo and the resulting imine intermediate was treated with sodium cyanoborohydride (1.98 g, 31.5 mmol) in 10 ml of glacial acetic acid for 4 h. The reaction mixture was quenched with water and neutralized with sodium bicarbonate powder, extracted with ethyl acetate and dried (sodium sulfate). Removal of all volatiles in vacuo afforded the crude 4-(Benzyloxyamino-methyl)-2,6-dichlorophenol (4.02 g) as a light yellow oil (M+1=298). This was converted to the title compound using the method described in example 1c (2.01 g, 59%) as a thick colorless oil. 1H NMR (400 MHz, CDCl3) δ 8.25 (s, 1H), 7.38 (m, 3H), 7.28 (m, 2H), 7.19 (s, 2H), 5.97 (s, 1H), 4.78 (s, 2H), 4.55 (s, 2H). M+1=326.

Workup

  1. customAll volatiles were removed in vacuo
  2. customThe reaction mixture was quenched with water and neutralized with sodium bicarbonate powder
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (sodium sulfate)
  5. customRemoval of all volatiles in vacuo

Sources & evidence

ORD record
ord-23c1518cf00b4a4fbc3ace8a0cabbbe4
Source dataset
uspto-grants-2005_11
Patent number
US06967220B2

Reaction notes

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