Hydrochloric Acid → 6-Amino-4-(3-methoxypropyl)-2H-1,4-benzoxazin-3(4H)-one

HRID 1092189Notes

Reaction equation

HRID 1092189 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11]2[CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=[CH:15][C:10]=2[O:9][CH2:8][C:7]1=[O:19].Cl>[Fe].[OH-].[Na+]>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]2[O:9][CH2:8][C:7](=[O:19])[N:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:11]=2[CH:12]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59817752HCID 59817752, compound

Product 1

HCID 549355996-Amino-4-(3-methoxypropyl)-2H-1,4-benzoxazin-3(4H)-one

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

At room temperature, an ethanolic solution (1100 mL) of 4-(3-methoxypropyl)-6-nitro-4H-benzo[1,4]oxazin-3-one (91.0 g, 0.34 mol) is treated with 6N HCl (170 mL, 1.02 mol of HCl) and powdered Fe (57.0 g, 1.02 mol), heated to 70° C., stirred for 15 h, cooled to 0° C., treated with 6N NaOH (250 mL), and filtered on a celite pad. The filtrate is diluted with CH2Cl2 (1000 mL), and the aq. layer is separated. The org. layer is washed with brine (2×300 mL), dried (Na2SO4), and evaporated to give 6-amino-4-(3-methoxypropyl)-4H-benzo[1,4]oxazin-3-one as light brown solid.

Workup

  1. temperaturecooled to 0° C.
  2. filtrationfiltered on a celite pad
  3. additionThe filtrate is diluted with CH2Cl2 (1000 mL)
  4. customthe aq. layer is separated
  5. washlayer is washed with brine (2×300 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-cf90412019e64de68c96945c6d34385e
Source dataset
uspto-grants-2012_03
Patent number
US08129411B2

Reaction notes

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