Water → Benzamide, 4-amino-5-chloro-N-(2-(cyclopropylamino)ethyl)-2-methoxy-

HRID 1085510Notes

Reaction equation

HRID 1085510 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([NH2:12])[C:9]([Cl:13])=[CH:8][C:4]=1[C:5]([OH:7])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:26]1([NH:29][CH2:30][CH2:31][NH2:32])[CH2:28][CH2:27]1.O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([NH2:12])[C:9]([Cl:13])=[CH:8][C:4]=1[C:5]([NH:32][CH2:31][CH2:30][NH:29][CH:26]1[CH2:28][CH2:27]1)=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 10240769N-(2-aminoethyl)cyclopropanamine

Product 1

HCID 3079596Benzamide, 4-amino-5-chloro-N-(2-(cyclopropylamino)ethyl)-2-methoxy-Yield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

8.06 g (0.04) mole of 2-methoxy-4-amino-5-chlorobenzoic acid and 7.12 g (0.044 mole) of carbonyldiimidazole are suspended in 80 ml of tetrahydrofuran and kept at 30° C. until the end of gas development. The solution of 5 g (0.05 mole) of cyclopropylethylenediamine in 15 ml of tetrahydrofuran is then slowly added, followed by keeping the temperature at 50° C. for 1 hour. After cooling down, the mixture is poured into water, the solid is removed by filtration and crystallized from alcohol, thus obtaining 13 g (91.7%) of 2-methoxy-4-amino-5-chloro-N-(2-(cyclopropylamino)-ethyl)-benzamide, having a melting point of 152°-3° C. Hydrochloride m.p.

Workup

  1. customkept at 30° C. until the end of gas development
  2. customat 50° C.
  3. customfor 1 hour
  4. temperatureAfter cooling down
  5. customthe solid is removed by filtration
  6. customcrystallized from alcohol

Sources & evidence

ORD record
ord-51421908554f4a8288c4657299f16049
Source dataset
uspto-grants-1991_04
Patent number
US05010108

Reaction notes

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