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Morpholine → 2-Nitro-4-morpholinocarbonylaniline

HRID 2731
Notes
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Reaction equation

HRID 2731 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>CN(C)C=O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8083MorpholineHCID 10868DicyclohexylcarbodiimideHCID 74115Benzoic acid, 4-amino-3-nitro-HCID 757711-Hydroxybenzotriazole

Product 1

HCID 205537522-Nitro-4-morpholinocarbonylaniline

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A mixture of 4-amino-3-nitrobenzoic acid (7.40 g), 1-hydroxybenzotriazole (6.59 g), dicyclohexylcarbodiimide (10.90 g), dry N,N-dimethylformamide (74 ml), and morpholine (4.3 ml) was stirred at room temperature for 2 hours. The insolubles were filtered out, and washed with N,N-dimethylformamide. The filtrate and the washing were combined, and concentrated to obtain a yellowish brown solid (16.01 g).

Workup

  1. filtrationThe insolubles were filtered out
  2. washwashed with N,N-dimethylformamide
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9c42e3fc562e485b97a64b0a8e60149a
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05731310

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes