Ammonia → HCID 68276549, compound

HRID 1050962Notes

Reaction equation

HRID 1050962 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([F:12])=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.C[N:15](C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.N.O1CCOCC1>C1COCC1>[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([F:12])=[CH:7][C:3]=1[C:4]([NH2:15])=[O:5]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 289741642-amino-5-fluoro-3-methylbenzoic acid

Product 1

HCID 68276549HCID 68276549, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-5-fluoro-3-methyl-benzoic acid (4.80 g, 28.4 mmol) in THF (60 ml) is added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (10.9 g, 56.8 mmol), 1-hydroxybenzotriazole hydrate (4.34 g, 28.4 mmol) and ammonia as 5 M solution in dioxane (283 ml, 142 mmol). The resulting slurry is stirred for 3 hours. The reaction mixture is filtered through Celite and washed with THF. The filtrate is evaporated and partitioned between water and ethyl acetate. The organic phase is dried over sodium sulfate and evaporated. The residue is crystallized from 2-propanol to afford 2-amino-5-fluoro-3-methyl-benzamide as beige crystals; HPLC/MS 1.68 min (B), [M+H] 169.

Workup

  1. filtrationThe reaction mixture is filtered through Celite
  2. washwashed with THF
  3. customThe filtrate is evaporated
  4. custompartitioned between water and ethyl acetate
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customevaporated
  7. customThe residue is crystallized from 2-propanol

Sources & evidence

ORD record
ord-78b12d4976024eb790fd21af79aa6770
Source dataset
uspto-grants-2016_07
Patent number
US09388142B2

Reaction notes

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