Hydrochloric Acid → N-(1-methylethyl)-(2-nitro-6-fluorophenyl)methylamine

HRID 583077Notes

Reaction equation

HRID 583077 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:5]=1[CH:6]=O)([O-:3])=[O:2].[CH:13]([NH2:16])([CH3:15])[CH3:14].[BH4-].[Na+].Cl>CO>[CH3:14][CH:13]([NH:16][CH2:6][C:5]1[C:8]([F:12])=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6363IsopropylamineHCID 4311764Sodium borohydrideHCID 135240432-Fluoro-6-nitrobenzaldehyde

Product 1

HCID 17777165N-(1-methylethyl)-(2-nitro-6-fluorophenyl)methylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-nitro-6-fluorobenzaldehyde(1.21 g, 7.16 mmol) in dry methanol (15 ml), was added isopropyl amine (1 ml, 11.4 mmol) and the mixture stirred for 24 hours at room temperature in argon atmosphere. Then NaBH4 (0.3 g, 7.9 mmol) was added and the reaction mixture was stirred for 36 hours. The suspension was neutralized by addition of HCl 5N, then was extracted with diethyl ether (1×100 ml) and dried over MgSO4 and evaporated at reduced pressure to afford N-(1-methylethyl)-(2-nitro-6-fluorophenyl)methylamine as a brown oil.

Workup

  1. stirringthe reaction mixture was stirred for 36 hours
  2. extractionwas extracted with diethyl ether (1×100 ml)
  3. dry with materialdried over MgSO4
  4. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-37b2d576b5c846d6b94415104c849d74
Source dataset
uspto-grants-1999_07
Patent number
US05929072

Reaction notes

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