4-amino-2-chloro-N,N-dimethylbenzamide → 3-Chloro-4-[(dimethylamino)methyl]aniline

HRID 1442644Notes

Reaction equation

HRID 1442644 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]([CH3:10])[CH3:9])=O)=[C:4]([Cl:13])[CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:13][C:4]1[CH:3]=[C:2]([NH2:1])[CH:12]=[CH:11][C:5]=1[CH2:6][N:8]([CH3:9])[CH3:10]

Participants

4

Reactant 2

HCID 109434804-amino-2-chloro-N,N-dimethylbenzamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 287218173-Chloro-4-[(dimethylamino)methyl]aniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Using the procedure of Example 1, Compound 13a2 was used in place of Compound 1j3 and carried forward to prepare 4-amino-2-chloro-N,N-dimethyl-benzamide Compound 13a3. 1M LAH (3.53 mL, 3.53 mmol) was added dropwise to a solution of Compound 13a3 (700 mg, 3.53 mmol) in THF (10 mL). After 10 minutes, the reaction was cooled to 0° C. and quenched with water. The mixture was extracted from ethyl ether with 1N HCl. The aqueous layer was adjusted to pH 10 with NaOH and the product was extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated to give 3-chloro-4-dimethylaminomethyl-phenylamine Compound 13a (150 mg) as a viscous brown oil. MS 185 (MH+).

Workup

  1. customquenched with water
  2. extractionThe mixture was extracted from ethyl ether with 1N HCl
  3. extractionthe product was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3c4d633cbbe7465d8921d4d323820346
Source dataset
uspto-grants-2010_02
Patent number
US07659284B2

Reaction notes

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