Water → 2',5-Dichloro-2-methylaminobenzhydrol

HRID 262915Notes

Reaction equation

HRID 262915 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:20])[C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[NH:18][CH3:19].O>O1CCCC1>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([OH:20])[C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[NH:18][CH3:19]

Participants

5

Reactant 3

HCID 962Water2×HCID 21833Benzophenone, 2',5-dichloro-2-methylamino-HCID 4311764Sodium borohydride

Product 1

HCID 124217352',5-Dichloro-2-methylaminobenzhydrolYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium borohydride (1.2 g) in tetrahydrofuran (10 ml), a solution of 2',5-dichloro-2-methylaminobenzophenone (3.12 g) in tetrahydrofuran (20 ml) is added dropwise. The resultant mixture is mixed with water (5 ml) and stirred at room temperature overnight. The reaction mixture is mixed with a small amount of water and evaporated under reduced pressure to remove the solvent. The residue is made to pH 8-9 with dilute hydrochloric acid and shaken with chloroform. The organic layer is dried and evaporated to give 2',5-dichloro-2-methylaminobenzhydrol (3.05 g). This substance is recrystallized from ether/n-hexane to give crystals melting at 105.5° to 106.5° C. The yield is 97.1%.

Workup

  1. customevaporated under reduced pressure
  2. customto remove the solvent
  3. stirringshaken with chloroform
  4. customThe organic layer is dried
  5. customevaporated

Sources & evidence

ORD record
ord-3c011174b6dc4b14a444dce0e9987a28
Source dataset
uspto-grants-1979_05
Patent number
US04154727

Reaction notes

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