Ammonia → 2-Amino-5-methylbenzamide

HRID 359532Notes

Reaction equation

HRID 359532 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4](O)=[O:5].O1CCCC1.[NH3:17]>O>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([NH2:17])=[O:5]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 762552-Amino-5-methylbenzoic acid

Product 1

HCID 103294362-Amino-5-methylbenzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 15 g of 2-amino-5-methylbenzoic acid, 16 g of 1,1-carbonyldiimidazole and 500 ml of tetrahydrofuran was stirred for 2 hours at room temperature and then saturated with anhydrous ammonia with ice bath cooling. After 24 hours, 50 ml of water was added and the mixture was concentrated under reduced pressure to a solid residue. This solid Was partially dissolved in 500 ml of dichloromethane and then washed with 200 ml of 0.1 N sodium hydroxide and 200 ml of water. The dichloromethane solution was dried and concentrated to a solid Which Was crystallized from ethyl acetate/hexane, giving 3.0 g of 2-amino-5-methylbenzamide as straw-colored crystals, mp 171°-174° C.

Workup

  1. waitAfter 24 hours
  2. concentrationthe mixture was concentrated under reduced pressure to a solid residue
  3. dissolutionThis solid Was partially dissolved in 500 ml of dichloromethane
  4. washwashed with 200 ml of 0.1 N sodium hydroxide and 200 ml of water
  5. dry with materialThe dichloromethane solution was dried
  6. concentrationconcentrated to a solid Which
  7. customWas crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e68c99d67c3e4389bcd7777e33b88a9f
Source dataset
uspto-grants-1991_03
Patent number
US05001157

Reaction notes

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