Water → Methyl 3-amino-5-morpholino-2-nitrobenzoate

HRID 539181Notes

Reaction equation

HRID 539181 reaction equation
[NH2:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]([CH:9]=[C:10](Cl)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[NH2:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]([CH:9]=[C:10]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 12165619Methyl 3-amino-5-chloro-2-nitrobenzoate

Product 1

HCID 58278827Methyl 3-amino-5-morpholino-2-nitrobenzoateYield 46.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of combined batches of methyl 3-amino-5-chloro-2-nitrobenzoate (39 g), morpholine (29.5 g) and K2CO3 (47 g) was stirred in DMF (200 ml) at 110° C. for 5 h. The mixture was cooled to room temperature and poured into water (1 L). It was extracted with EtOAc (500 mL×3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in-vacuo to afford the desired product as a yellow solid (22 g, yield 46%). 1H NMR (300 MHz, CDCl3): δ ppm 3.31 (t, 4H, J=4.8 Hz), 3.82 (t, 4H, J=4.8 Hz), 3.89 (s, 3H), 6.03 (d, 1H, J=2.4 Hz), 6.34 (d, 1H, J=2.4 Hz); LC-MS: m/e=282 [M+1]+.

Workup

  1. extractionIt was extracted with EtOAc (500 mL×3)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-c15a3d2397d245b785caba99031b66c5
Source dataset
uspto-grants-2014_10
Patent number
US08865912B2

Reaction notes

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