HCID 13227200, compound → HCID 20352627, compound

HRID 1283400Notes

Reaction equation

HRID 1283400 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([C:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])=[CH:5][C:4]=1[N+:16]([O-])=O>N.O>[NH2:16][C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][C:3]=1[O:2][CH3:1])[C:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8]

Participants

4

Reactant 1

HCID 13227200HCID 13227200, compound

Product 1

HCID 20352627HCID 20352627, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 962WaterSolvent

Procedure

A solution of 3-(4-methoxy-3-nitrobenzoyl) propionic acid (10.5 g.) in 5N ammonia solution (150 ml.) was added in one portion to a stirred hot (90°C) solution of hydrated ferrous sulphate (90 g.) in water (210 ml.) and stirring was continued for 10 minutes more. The hot mixture was filtered through Hyflo and the filtrate was concentrated to 50 ml. volume and neutralised with acetic acid. The mixture was cooled, the precipitated solid collected and purified by crystallisation from dilute methanol to yield the amine, (5.5 g.), m.p. 136°-137°C.

Workup

  1. filtrationThe hot mixture was filtered through Hyflo
  2. concentrationthe filtrate was concentrated to 50 ml
  3. temperatureThe mixture was cooled
  4. customthe precipitated solid collected
  5. custompurified by crystallisation from dilute methanol

Sources & evidence

ORD record
ord-ead5d35e067c4b05b9b6fe1c898156a1
Source dataset
uspto-grants-1976_08
Patent number
US03975388

Reaction notes

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