Phenylacetic Acid → HCID 13971354, compound

HRID 1650670Notes

Reaction equation

HRID 1650670 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([OH:9])[C:5]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][C:3]=1[CH3:14].[C:15]1([CH2:21][C:22](O)=O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:21]([C:22]1[NH:8][C:7]2[C:6]([OH:9])=[C:5]([C:10]([CH3:11])([CH3:13])[CH3:12])[CH:4]=[C:3]([CH3:14])[C:2]=2[N:1]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 999Phenylacetic AcidHCID 23052379HCID 23052379, compound

Product 1

HCID 13971354HCID 13971354, compoundYield 51.1%

Procedure

A mixture of 2,3-diamino-4-hydroxy-5-tert-butyltoluene (Description 11) (prepared from 12 g of 2,3-dinitro-4-hydroxy-5-tert-butyltoluene) and phenylacetic acid (30 g) was heated for 1 h at 120°-130° C. under nitrogen. The reaction product was extracted with chloroform, washed with 10% sodium carbonate, water, and dried (Na2SO4). The chloroform solution was evaporated to dryness in vacuo, and recrystallised from chloroformethylacetate-pentane to afford the title compound (9.3 g), m.p. 226°-228° C.

Workup

  1. temperaturewas heated for 1 h at 120°-130° C. under nitrogen
  2. extractionThe reaction product was extracted with chloroform
  3. washwashed with 10% sodium carbonate, water
  4. dry with materialdried (Na2SO4)
  5. customThe chloroform solution was evaporated to dryness in vacuo
  6. customrecrystallised from chloroformethylacetate-pentane

Sources & evidence

ORD record
ord-c321913c126146c0b416d84f898776b9
Source dataset
uspto-grants-1990_05
Patent number
US04925853

Reaction notes

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