Hydrochloric Acid → HCID 86683436, compound

HRID 579471Notes

Reaction equation

HRID 579471 reaction equation
[CH:1]([C:3]1[C:4]([OH:27])=[C:5]([O:25][CH3:26])[CH:6]=[C:7]2[C:12]=1[O:11][C:10](=[O:13])[C:9]([CH2:14][C:15]([NH:17][CH2:18][CH2:19][O:20]COC)=[O:16])=[C:8]2[CH3:24])=[O:2].Cl>C(Cl)(Cl)Cl>[CH:1]([C:3]1[C:4]([OH:27])=[C:5]([O:25][CH3:26])[CH:6]=[C:7]2[C:12]=1[O:11][C:10](=[O:13])[C:9]([CH2:14][C:15]([NH:17][CH2:18][CH2:19][OH:20])=[O:16])=[C:8]2[CH3:24])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86683437HCID 86683437, compound

Product 1

HCID 86683436HCID 86683436, compoundYield 11.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-(8-Formyl-7-hydroxy-6-methoxy-4-methyl-2-oxo-2H-chromen-3-yl)-N-(2-(methoxymethoxy)ethyl)acetamide (400 mg, 1.06 mmol) in CHCl3 (40 mL) and conc.HCl (20 mL) was heated to reflux for 1 h, and then concentrated to give the residue and purified by prep.HPLC to give 2-(8-Formyl-7-hydroxy-6-methoxy-4-methyl-2-oxo-2H-chromen-3-yl)-N-(2-hydroxyethyl)acetamide (40 mg, 11.3%) as yellow solid. 1H NMR: (CDCl3, 400 MHz) δ 12.47 (d, J=0.4 Hz, 1H, OH), 10.02 (s, 1H, CHO), 7.22 (s, 1H, ArH), 6.60 (br, 1H, NH), 4.63 (s, 2H, CH2), 3.97 (s, 3H, OCH3), 3.60 (t, J=5.4 Hz, 4H, CH2), 3.45 (m, 2H, CH2), 3.36 (d, J=0.4 Hz, 2H, CH2), 2.57 (s, 3H, CH3); MS [ESI, MH+]: 380.2.

Workup

  1. temperatureto reflux for 1 h
  2. concentrationconcentrated
  3. customto give the residue
  4. custompurified by prep.HPLC

Sources & evidence

ORD record
ord-fe0a55972d664ffc8fc01de81831d6ea
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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