Methanol → Methyl 3-(6-amino-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl)benzoate

HRID 1723238Notes

Reaction equation

HRID 1723238 reaction equation
O.[OH-].[Li+].C([NH:11][C:12]1[CH:13]=[CH:14][C:15]2[O:20][CH2:19][CH2:18][N:17]([CH2:21][C:22]3[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=3)[C:25]([O:27][CH3:28])=[O:26])[C:16]=2[CH:32]=1)(=O)CCCCC.CO.O1CCCC1>O.C(O)(=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[NH2:11][C:12]1[CH:13]=[CH:14][C:15]2[O:20][CH2:19][CH2:18][N:17]([CH2:21][C:22]3[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=3)[C:25]([O:27][CH3:28])=[O:26])[C:16]=2[CH:32]=1

Participants

9

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 23365863Methyl 3(6-Hexanamido-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl)benzoate

Product 1

HCID 54048005Methyl 3-(6-amino-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl)benzoateYield 58.5%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Lithium hydroxide monohydrate (0.2 g.) in water (5 ml.) was added to a stirred solution of methyl 3-(6-hexanamido-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl)benzoate (ca. 400 mg.) in 1:1 v/v methanol: tetrahydrofuran (10 ml.). When TLC (solvent system 80:20:2 v/v/v toluene:ethyl acetate:acetic acid) indicated complete disappearance of ester, the mixture was diluted with water, filtered to remove any solids, and carefully acidified with 1N hydrochloric acid. The precipitate was isolated by filtration and recrystallized from a mixture of methanol and water to give the title compound (0.176 g., 46% overall yield from amino ester (X)) as an off-white solid, m.p. 167°-171° C. (hemihydrate).

Workup

  1. filtrationfiltered
  2. customto remove any solids
  3. customThe precipitate was isolated by filtration
  4. customrecrystallized from a mixture of methanol and water

Sources & evidence

ORD record
ord-d3614d26e9134a69bd5f603df04d9cef
Source dataset
uspto-grants-1989_08
Patent number
US04859692

Reaction notes

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