Sodium Hydroxide → HCID 21506055, compound

HRID 918650Notes

Reaction equation

HRID 918650 reaction equation
[CH2:1]([O:8][C:9]1[CH:31]=[CH:30][C:12]([O:13][C:14]2[C:22]([S:23](=[O:26])(=[O:25])[NH2:24])=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]=2[N+:27]([O-])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[H][H]>O.[Pt]=O>[NH2:27][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([S:23](=[O:26])(=[O:25])[NH2:24])[C:14]=1[O:13][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:31][CH:30]=1)[C:18]([OH:20])=[O:19]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21506032HCID 21506032, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21506055HCID 21506055, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 962WaterSolvent

Procedure

A suspension of 4-(4-benzyloxyphenoxy)-3-nitro-5-sulphamyl-benzoic acid (10 g) in water (250 ml) was adjusted to pH 11 by addition of 1N sodium hydroxide. The resulting solution was hydrogenated at room termperature and at 1.1 atmospheres hydrogen pressure after addition of a platinum oxide catalyst (0.4 g). After the hydrogen uptake had become negligible, the catalyst was removed by filtration, and the 3-amino-4-(4-benzyloxyphenoxy)-5-sulphamyl-benzoic acid was precipitated by adjusting the filtrate to pH 2.5 by addition of 4N hydrochloric acid. After recrystallization from aqueous ethanol and drying, the compound was obtained with a melting point of 264°-265°C.

Workup

  1. customthe catalyst was removed by filtration
  2. customthe 3-amino-4-(4-benzyloxyphenoxy)-5-sulphamyl-benzoic acid was precipitated
  3. additionby addition of 4N hydrochloric acid
  4. customAfter recrystallization from aqueous ethanol
  5. customdrying
  6. customthe compound was obtained with a melting point of 264°-265°C.

Sources & evidence

ORD record
ord-494de1ae923342a8b2abbf63515074dc
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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