Water → 4-(Morpholine-4-carbonyl)aniline

HRID 1249313Notes

Reaction equation

HRID 1249313 reaction equation
O.[N+](C1C=CC(C(Cl)=O)=CC=1)([O-])=O.N1CCOCC1.[N+:20]([C:23]1[CH:36]=[CH:35][C:26]([C:27]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:28])=[CH:25][CH:24]=1)([O-])=O>O1CCOCC1.[Pd]>[NH2:20][C:23]1[CH:36]=[CH:35][C:26]([C:27]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:28])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 85024-Nitrobenzoyl chlorideHCID 220838(Morpholin-4-yl)(4-nitrophenyl)methanone

Product 1

HCID 5778154-(Morpholine-4-carbonyl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

The above dyes can be prepared by a conventional method. For example, the dye (1) given in Table 1, which is a red water-soluble dye, can be prepared as follows: One mole of 4-nitrobenzoyl chloride is allowed to react with 2 moles of morpholine in dioxane at a temperature below room temperature, so that 4-nitrobenzoylmorpholine (m.p. 108° 109° C.) is obtained. The thus obtained nitro compound is reduced in the presence of a 5%Pd-C catalyst to produce 4-aminobenzoylmorpholine. This is subjected to diazotization by a conventional method to produce a diazonium compound, which is then coupled with H-acid in an alkaline solution, followed by subjecting it to acidic precipitation, so that the dye (I) in Table 1 is obtained.

Workup

  1. customThe above dyes can be prepared by a conventional method
  2. customcan be prepared
  3. customis obtained

Sources & evidence

ORD record
ord-099e0632ad6f449f91123bb3dad47b42
Source dataset
uspto-grants-1986_12
Patent number
US04631085

Reaction notes

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