Hydrochloric Acid → HCID 66697278, compound

HRID 2096857Notes

Reaction equation

HRID 2096857 reaction equation
C([Mg]Cl)(C)(C)C.[Cl:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH2:16][C:17]([OH:19])=O.COC([C:24]1[CH:35]=[CH:34][C:27]2[N:28]([CH3:33])[C:29](=[O:32])[CH2:30][O:31][C:26]=2[CH:25]=1)=O.Cl>C(OCC)C.C1COCC1.O>[Cl:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH2:16][C:17]([C:24]1[CH:35]=[CH:34][C:27]2[N:28]([CH3:33])[C:29](=[O:32])[CH2:30][O:31][C:26]=2[CH:25]=1)=[O:19]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 42091322-(2-Chloro-4-methoxyphenyl)acetic acidHCID 10560922methyl 4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylateHCID 178418310HCID 178418310, compound

Product 1

HCID 66697278HCID 66697278, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M solution of tert-butylmagnesium chloride (CAS Reg. No. 677-22-5) in diethyl ether (2.1 ml) was added to 2-chloro-4-methoxyphenylacetic acid (CAS 91367-09-8) (200 mg) in THF (5 ml). The mixture was stirred at room temperature for 30 min. A solution of 4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-7-carboxylic acid methyl ester (200 mg, CAS Reg. No. 201294-27-1) in THF (3 ml) was added and the resulting mixture was stirred overnight. Aqueous HCl (25%, 0.5 ml) and water (10 ml) were added and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, 10 to 50% EtOAc/heptane) to give the title compound (100 mg) as a light yellow solid. MS (m/e)=346.1 [M+H+].

Workup

  1. stirringthe resulting mixture was stirred overnight
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated to an oil
  5. customThe residue was purified by flash chromatography (SiO2, 10 to 50% EtOAc/heptane)

Sources & evidence

ORD record
ord-6ea0a27be7ad479fb270a79343497548
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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