Phosphorus oxybromide → HCID 85866300, compound

HRID 1365093Notes

Reaction equation

HRID 1365093 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11](O)=O.P(Br)(Br)([Br:20])=O>>[Br:20][C:1]1[C:2]2[C:3]([N:8]=[C:9]3[C:17]=1[CH:16]=[CH:15][CH:14]=[C:10]3[CH3:11])=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

3

Reactant 2

HCID 24613Phosphorus oxybromideHCID 85510Anthranilic acid, N-(o-tolyl)-

Product 1

HCID 85866300HCID 85866300, compoundYield 85%

Conditions

Temperature
120 °C

Procedure

2-(2′-Methylphenylamino)benzoic acid 7 (1.0 g, 4.4 mmol) was suspended in 11.0 g (38 mmol) of phosphorus oxybromide, and the mixture was heated to 120° C. for 2 hours. Excess phosphorus oxybromide was removed by distillation and the residual solution was poured into a 1:1 mixture of aqueous ammonium hydroxide:CH2Cl2. The CH2Cl2 solution was separated, dried, filtered, and the combined organic layers were dried in vacuo to give 9 (1.0 g, 85%) as a yellow powder. 1H-NMR δ=2.94 (s, 3H), 7.53 (dd, J=8.5 Hz, J=8.8 Hz, 1H), 7.59-7.69 (m, 2H), 7.78 (ddd, J=1.4 Hz, J=8.5 Hz, J=8.5 Hz, 1H), 8.28 (dd, J=8.5 Hz, J=8.5 Hz, 2H), 8.43 (dd, J=1.4 Hz, J=8.8 Hz, 1H). 13C-NMR δ=19.48, 126.37, 128.49, 128.76, 129.07, 129.28, 129.72, 130.95, 131.15, 131.88, 135.87, 138.12, 148.43, 148.71. Anal. calcd. for C14H10NBr: C, 61.79; H, 3.70; N, 5.15. Found: C, 61.40; H, 3.72; N, 5.05.

Workup

  1. customExcess phosphorus oxybromide was removed by distillation
  2. additionthe residual solution was poured into a 1:1 mixture of aqueous ammonium hydroxide
  3. customThe CH2Cl2 solution was separated
  4. customdried
  5. filtrationfiltered
  6. customthe combined organic layers were dried in vacuo

Sources & evidence

ORD record
ord-feeba99bddcc44bc9dd594f131a9aa08
Source dataset
uspto-grants-2011_02
Patent number
US07888509B2

Reaction notes

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