Aniline → HCID 131716908, compound

HRID 1493639Notes

Reaction equation

HRID 1493639 reaction equation
NC1C=CC=CC=1.Cl.[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][C:18]2[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=2)=[CH:12][CH:11]=1.C(=O)(O)[O-].[Na+].Cl[CH2:31][C:32]([O:34][CH3:35])=[O:33]>C(#N)C.O>[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][C:18]2[CH:19]=[C:20]([NH:24][CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH:21]=[CH:22][CH:23]=2)=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 7295Methyl chloroacetateHCID 516892Sodium BicarbonateHCID 19829889HCID 19829889, compound

Product 1

HCID 131716908HCID 131716908, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of the aniline (Intermediate 82, 20 g, 94 mmol), sodium bicarbonate (11.8 g, 141 mmol) and methyl chloroacetate (9.1 ml, 103 mmol) in acetonitrile (30 ml) was heated at 90°-100° for 24 h. Water (200 ml) was added and the mixture was extracted with ethyl acetate (2×100 ml). The combined extracts were washed with 2N hydrochloric acid (2×100 ml), water (2×100 ml) and brine (100 ml) before drying (Na2SO4) and evaporating to an orange solid. Trituration with ether, followed by evaporation of the triturate gave the title compound (Intermediate 83) as a pale grey solid (16 g; 60%), m.p. 78°-80°.

Workup

  1. temperaturewas heated at 90°-100° for 24 h
  2. extractionthe mixture was extracted with ethyl acetate (2×100 ml)
  3. washThe combined extracts were washed with 2N hydrochloric acid (2×100 ml), water (2×100 ml) and brine (100 ml)
  4. dry with materialbefore drying (Na2SO4)
  5. customevaporating to an orange solid
  6. customTrituration with ether, followed by evaporation of the triturate

Sources & evidence

ORD record
ord-72945bd4bf664dad8144bef12f2d277c
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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