Water → 3-(o-Carboxyphenylthio)-4-hydroxybenzonitrile

HRID 977908Notes

Reaction equation

HRID 977908 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[OH:19])[CH:14]=O)([OH:3])=[O:2].Cl.[NH2:21]O.C([O-])=O.[Na+].O>C(O)=O>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[OH:19])[C:14]#[N:21])([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium FormateHCID 133386863-(o-Carboxyphenylthio)-4-hydroxybenzaldehyde

Product 1

HCID 133386873-(o-Carboxyphenylthio)-4-hydroxybenzonitrile

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Reflux 91.3 gm of the aldehyde of Step D, 27.4 gm of hydroxylamine hydrochloride and 41.9 gm of sodium formate in 900 cc of formic acid (98-100%) for 11/4 hours. Cool the mixture and pour into 21/2 l. of cold water. Separate the precipitate, wash with water and dry in vacuo at 75° C. The material is sufficiently pure for utilization in the subsequent step.

Workup

  1. temperatureCool the mixture
  2. additionpour into 21/2 l
  3. customSeparate the precipitate
  4. washwash with water
  5. customdry in vacuo at 75° C

Sources & evidence

ORD record
ord-b8d0728ddf864306a38aee09e6ca552f
Source dataset
uspto-grants-1987_05
Patent number
US04663307

Reaction notes

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