Acetic Acid → HCID 9945970, compound

HRID 1063875Notes

Reaction equation

HRID 1063875 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:19])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[CH:5]=O.Cl.[NH2:21][OH:22].C([BH3-])#N.[Na+].[C:27]([OH:30])(=O)C>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:19])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[CH2:5][N:21]([OH:22])[CH:27]=[O:30]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 443297Hydroxyamine hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 22277850HCID 22277850, compound

Product 1

HCID 9945970HCID 9945970, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3,5-dichloro-4-(4-methoxyphenoxy)benzaldehyde (170 mg, 0.572 mmol) and hydroxylamine hydrochloride (48 mg, 0.687 mmol) in 1 ml of pyridine was stirred for 1 h then all volatiles were removed in vacuo. The resulting imine intermediate was treated with sodium cyanoborohydride (122 mg, 1.944 mmol) in 2 ml of glacial acetic acid for 5 h. The reaction mixture was then quenched with water and neutralized with sodium bicarbonate powder, extracted with ethyl acetate and dried (sodium sulfate). The resulting 3,5-dichloro-N-hydroxy-4-(4-methoxyphenoxy)benzyl amine was converted to the title compound using the method described in example 1c (50 mg, 26%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 8.06 (s, 1H), 7.34 (s, 2H), 6.82 (d, j=8.8 Hz, 2H), 6.76 (d, j=8.8 Hz, 2H), 4.64 (s, 2H), 3.76 (s, 3H). M+1=342.

Workup

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

Sources & evidence

ORD record
ord-38c7673fbf4547d5978bc0645ed095aa
Source dataset
uspto-grants-2005_11
Patent number
US06967220B2

Reaction notes

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