Sodium Bicarbonate → HCID 11684057, compound

HRID 379158Notes

Reaction equation

HRID 379158 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=1.Cl.[CH3:23][N:24]1[CH2:31][CH2:30][CH:29]=[C:26]([CH2:27]Cl)[CH2:25]1.C(=O)(O)[O-:33].[Na+]>O1CCCC1>[Br:21][C:17]1[CH:16]=[C:15]([NH:14][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:27]([C:26]4[CH2:25][N:24]([CH3:23])[CH2:31][CH2:30][CH:29]=4)=[O:33])[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:12]#[N:13])[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrileHCID 14615850HCID 14615850, compound

Product 1

HCID 11684057HCID 11684057, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1 g (2.95 mmol) of 6-amino-4-[(3-bromophenyl)amino]-quinoline-3-carbonitrile and 1.9 g (14.7 mmol) of dissopropylethylamine was strirred in 19 ml of tetrahydrofuran and solid N-methyl-1,2,5,6-tetrahydronicotinyl chloride hydrochloride was added portionwise at 0° C. After stirring 1 hr at 0° C. and 2 hr at room temperature, the mixture was poured into saturated sodium bicarbonate and extracted with ethylacetate. The solution was dried over magnesium sulfate. Sovent was removed and the residue was recrystalized from methanol-ethylacetate giving 0.92 g of a yellow powder: mass spectrum (electrospray, m/e,): M+H 462.4, 464.4.

Workup

  1. extractionextracted with ethylacetate
  2. dry with materialThe solution was dried over magnesium sulfate
  3. customSovent was removed
  4. customthe residue was recrystalized from methanol-ethylacetate giving 0.92 g of a yellow powder

Sources & evidence

ORD record
ord-376ef4a712ef49a9b45ff5f32e9f344e
Source dataset
uspto-grants-2001_10
Patent number
US06297258B1

Reaction notes

Loading…